Research: Science and Education
The Aromaticity of Pericyclic Reaction Transition States
Henry S. Rzepa
Department of Chemistry, Imperial College London, South Kensington Campus, Exhibition Road, London, SW7 2AY,
United Kingdom; h.rzepa@imperial.ac.uk
The electronic theory of organic chemistry underpins
one of the most interesting, but subtle, concepts currently
taught in the subject, that of the “stereoelectronic control”
of reactions. For a particular mechanistic type known as the
pericyclic reaction, other concepts fundamental to organic
chemistry such as stereochemistry, chirality, aromaticity, and
quantum mechanics are interwoven. The impact of this fu-
sion of ideas on organic chemistry has been recognized with
the award of a Nobel Prize in 1981 to one the original archi-
tects, Roald Hoffmann (the other, Robert Woodward, had
died in 1979 and was ineligible to receive the prize posthu-
mously). In this article, these diverse concepts are brought
together via an illustration of transition states for one spe-
cific pericyclic reaction that played a key role in the first ex-
perimental synthesis of a new type of molecule, a Möbius
annulene.
The discoverer of the electron, J. J. Thomson, was among
the first to also develop models using the electron to account
for chemical bonding. In 1921, just before the dawn of quan-
tum mechanics, he published (1) an exploration of the bond-
ing for the archetypal aromatic molecule, benzene. In his
scheme, each C⫺C region in this species was bonded using
three electrons (Figure 1). Reading his description, it is evi-
dent that the electron was still very much regarded as a point
particle and that there was yet hardly a glimmer of recogni-
tion that the group of three electrons might have differing
spatial (3D) characteristics. The advent of quantum mechan-
ics and the formulation of the Schrödinger wave equation
brought with it an understanding of the spatial and energetic
properties of electrons, more formally described by wavefunc-
tions. This allowed a segregation of two of Thomson’s three
electrons in each C⫺C region of benzene into a low energy
σ set, which form what is now called a C⫺C σ bond, and
the third electron as contributing to a spatially distinct band
of six rather higher-energy electrons not directly associated
with any single C⫺C bond but with the aromatic ring itself,
and which became widely known as the aromatic π sextet
(Figure 1) (2).
Figure 1. (left) Thomson’s three-electron bonds in benzene and (right)
the segregation of these 18 electrons into six pairs of two-electron
C⫺C bonds and a π aromatic sextet following Hückel.
www.JCE.DivCHED.org • Vol. 84 No. 9 September 2007
W
The first person to formalize this separation was Erich
Hückel in 1930 (3). He used the new theory of quantum
mechanics to derive a principle of σ–π separability, which
he used to explain the restricted rotation in alkenes. Hückel
in 1931 extended this concept to benzene, predicting par-
ticular stability for a cyclic arrangement of six π electrons in
wavefunctions (molecular orbitals) formed by overlapping
carbon-centered 2p atomic orbitals into a planar ring. The
concept of atomic orbitals had previously been derived by
solving the quantum mechanical Schrödinger wave equation
for a hydrogen atom. It took little while longer for organic
chemists to properly generalize and understand Hückel theory
as a useful, albeit approximate, theoretical basis for the wider
concept of aromaticity. The emergent Hückel rule (first suc-
cinctly coined not by Hückel himself but by William Doering
as late as 1951; ref 3) is conventionally applied to planar
molecules containing cyclically conjugated π electrons (re-
ferred to below as having Hückel topology) and is now enu-
merated:
1. 4n + 2 (where n is an integer) π electrons, thermally
(closed shell with all molecular orbitals doubly occu-
pied) aromatic and stable
2. 4n π electrons, photochemically (open shell, with two
molecular orbitals each occupied by a single electron)
aromatic and stable
3. 4n π electrons, thermally anti-aromatic and less stable
4. 4n + 2 π electrons, photochemically anti-aromatic and
less stable.
Rules 2 and 4 were added in the 1960s, as the quantum
mechanical understanding of photochemically excited states
(open shell systems with two molecular orbitals each singly
occupied) developed. These nowadays are regarded as a much
more approximate heuristics than the thermal rules 1 and 3.
A particularly characteristic feature of what might be
called “classical” aromatic chemistry is the planarity (two-di-
mensionality) of the ring. When the representation of a pla-
nar molecule is reflected in a mirror, the 3D arrangement of
atoms can be exactly superimposed on the original unreflected
set, such molecules are said to be achiral. A small class of
aromatic molecules are forced to be nonplanar for steric rea-
sons. A good example are the helicenes, which adopt a heli-
cal arrangement of the rings (Figure 2). When reflected in a
mirror plane such a helicene cannot be superimposed upon
the original and the system is said to exist as a pair of chiral
or dissymmetric enantiomers. Of course, aromatic molecules
can support chiral groups as substituents on the rings, but
we exclude this class in our argument here, since we are con-
cerned only with the nature of the aromatic structures them-
selves.
• Journal of Chemical Education 1535
 Research: Science and Education
Figure 2. A heptahelicene and its non-superimposable mirror image.
Figure 3. Heilbronner’s suggestion for a π Möbius conjugated sys-
tem obtained by π electrons located in molecular orbitals resulting
from 2p atomic orbitals distributed around a Möbius strip bearing
a single half-twist, rather than a planar Hückel ring bearing no
twist in the orbital basis.
Figure 4. Frost–Musulin and Zimmerman mnemonics for aromatic-
ity selection rules. A six-sided polygon is shown for the Hückel case
to coincide with the example shown later in Scheme III (solid ar-
rows) and an eight-sided polygon is shown for the Möbius case to
coincide with the dashed arrows in Scheme III.
1536 Journal of Chemical Education • Vol. 84 No. 9 September 2007
Hückel and Möbius Aromatics
Thus these two great concepts of organic chemistry, aro-
maticity and chirality, remained mostly exclusive. Edgar
Heilbronner in 1964 (4) and Howard Zimmerman in 1966
(5) both came up with radical new suggestions that allow a
fusion of these concepts. Rather than distributing π electrons
in a planar ring comprising precisely parallel overlap of 2p
atomic orbitals, Heilbronner considered what might happen
if this array were instead distributed along a Möbius strip
bearing a single half (left or right) twist (Figure 3).
Heilbronner applied Hückel’s equations (3) to such a cy-
clic Möbius ring, finding that a 4n π-electron system would
be a closed-shell species like benzene, with no loss of π-elec-
tron resonance energy compared to the equivalent untwisted
Hückel ring. A closed-shell 4n + 2 π electron Möbius ring
was predicted to be less stable than the untwisted Hückel
counterpart.
Like Hückel before him, Heilbronner did not derive a
succinct rule of aromatic stability from these results.
Zimmerman (5) was the first to clearly associate the π-elec-
tron stability of such Möbius rings with an inversion of the
aromaticity rules 1 and 2 above. Specifically, populations of
4n π electrons result in closed-shell (two electrons per π en-
ergy level) molecules if the 2p atomic orbitals are distributed
along a Möbius strip (rule 1 inverted), whereas 4n + 2 π-
electrons will adopt an open-shell (photochemical) distribu-
tion in which two of the electrons will now each occupy a
separate molecular orbital (rule 2 inverted) (5). By adding a
corollary for the anti-aromatic cases, rules 5–8 to comple-
ment 1–4 can be listed:
5. 4n electrons, thermally (closed shell) aromatic and
stable with Möbius π topology
6. 4n + 2 electrons, photochemically (open shell) aro-
matic and stable with Möbius π topology
7. 4n + 2 electrons, thermally (closed shell) less stable
with Möbius π topology
8. 4n π electrons, photochemically (open shell) less stable
with Möbius π topology.
A useful visual mnemonic first proposed by Frost and
Musulin (6) for orbital energies of π-electron rings based on
inscribing a polygon with one vertex down for the Hückel
rules, was memorably extended by Zimmerman (5) to Möbius
systems by redrawing the polygons with one edge down (Fig-
ure 4).
Another aspect of Möbius systems that was not directly
commented upon by Heilbronner is that a Möbius strip bear-
ing one half-twist is also chiral, in the sense noted above for
the heptahelicene molecule (Figure 2). An ideal Möbius strip
has only a C2 axis of symmetry present. The specific absence
of a plane of symmetry means the mirror image of a Möbius
strip is not superimposable upon the original. In contrast,
an ideal planar aromatic molecule of the Hückel type does
have at least one plane of symmetry, referred to here as a Cs
mirror plane, which means that its mirror image is superim-
posable with the original. Thus in Möbius ringed molecules,
we do now have a fusion of two seminal concepts in organic
chemistry, that of aromaticity and of chirality!
• www.JCE.DivCHED.org

Scheme I. An example from Woodward and Hoffmann illustrating
how the outcome of a pericyclic reaction depends on
stereoelectronic control mediated by heat or by light (7).
The next intellectual leap involves a class of organic re-
actions known as pericyclic and the recognition by Wood-
ward and Hoffmann (7) that the stereochemical outcome of
such reactions was quantum mechanical in origin (Scheme
I). The original Woodward and Hoffmann argument was
based on the symmetries of a subset of the molecular orbit-
als called frontier orbitals. This analysis was extended by
Longuet-Higgins and Abrahamson (7) to a more formal dia-
gram showing the correlation of the symmetries of the reac-
tants and product molecular orbitals and particularly whether
either of the C2 or the Cs symmetry elements noted above
were preserved during the course of the pericyclic reaction.
A difficulty in applying such symmetry arguments was the
experimental observation that most pericyclic reactions in-
volved no formal symmetry at all! This difficulty can be over-
come by the following procedure:
• By considering only the (cyclic) transition state for the
pericyclic reaction, one can pose the question: is it aro-
matic or not? The advantage is that the aromaticity of
a system is robust to minor, desymmetrizing pertur-
bations caused by the presence of substituents and
other nonparticipating groups.
• By equating (ideal) C2 transition-state symmetry with
Möbius topology and (ideal) Cs symmetry with Hückel
topology, one can now apply the aromaticity rules
listed above to the transition state.
The first person to associate the π-electron stability (aro-
maticity) of Möbius and Hückel rings with the “allowed” or
“forbidden” nature of the transition states for pericyclic re-
actions was Zimmerman (5), via the mnemonic shown above
(Figure 4). Thus the preferred outcome of a pericyclic reac-
tion can be predicted by analyzing whether the transition state
might exhibit Hückel or Möbius aromaticity (7). This simple
statement carries some of the most profound and powerful
concepts in modern organic chemistry.
www.JCE.DivCHED.org • Vol. 84 No. 9 September 2007
Research: Science and Education
Quantifying Aromaticity
Before introducing a pericyclic reaction that can be used
to embody and illustrate these concepts, one more tool is
needed. How does one quantify, or measure, the concept
known as “aromaticity”. Although much of the discussion
above is couched in terms of the (theoretical) π-electron en-
ergy, it turns out that accurate measures of aromaticity in
terms of (theoretical or experimental) energies are frustrat-
ingly elusive. Many other criteria have been proposed, and
the consensus seems to be that no single experimental mea-
surement or theoretical calculation can fully, accurately, and
uniquely represent aromaticity. It is also evident that experi-
mentally measuring aromaticity for a transition state will be
particularly difficult given its very short lifetime (∼10᎑15 s)!
Instead, recourse has to be taken to a quantum mechanical
calculation rather than direct measurement. Instead of using
energies, two other property calculations are used here for
this purpose:
1. The first is inspection of the C⫺C (or C⫺heteroatom)
bond lengths around the periphery of the ring formed
by the pericyclic transition state. For relatively small
sized rings (less than 14 carbon atoms), aromaticity
can be related to the degree of alternation in the bond
lengths; no alternation indicates a high degree of aro-
maticity (and implied stability), whereas partitioning
into short (double) and long (single) bond lengths in-
dicates no aromaticity or even anti-aromaticity. This
measure is often expressed as ∆r, the difference between
the longest and the shortest C⫺C bond in the cycle,
which typically has a value between 0.00 and 0.04 Å
for an aromatic ring and equal to 0.1 Å for a non-
aromatic or anti-aromatic ring.
2. The second measure was introduced by Paul Schleyer
(8) and was based on the predicted magnetic proper-
ties of the ring current induced by aromatic electrons.
One measurable property of aromatic molecules is the
NMR chemical shift of, for example, protons exposed
to such ring currents, which have values characteristic
of “aromaticity” (7–8 ppm relative to tetramethyl-
silane). To produce a more specific, single metric of
aromaticity, Schleyer proposed instead a calculated
property he termed the nucleus independent chemi-
cal shift or NICS(0). This property was to be com-
puted at the center of the ring whose aromaticity
needed to be estimated. By comparison with benzene,
a value of about ᎑10 ppm would be deemed aromatic,
a value of around zero would be non-aromatic, while
a positive value of , for example, +20 would be deemed
anti-aromatic. Both these metrics will be used in dis-
cussing the example introduced below.
Electrocyclic Ring-Closing Reaction
and the Synthesis of a [16] Möbius Annulene
The example we have chosen is derived from a remark-
able recent synthesis inspired by Heilbronner’s 1964 proposal.
From rule 5 above, one can see that a 4n cyclic aromatic (or
annulene) is predicted to be Möbius aromatic. Herges (9) and
colleagues Ajami, Oeckler, and Simon set out to synthesize a
• Journal of Chemical Education 1537
 Research: Science and Education
Scheme II. Herges’ scheme for the synthesis of a [16] Möbius ring. Bonds marked with b carry a benzo substituent, omitted for clarity.
Isomer F with a C2 symmetry axis is the first known Möbius annulene. Note that either the solid or dashed arrows are used in E to form the
resonance structures of F.
[16] Möbius annulene (n = 4) in the laboratory with the pur-
pose of subjecting it to experimental tests to see whether it
really were aromatic. The synthetic route is presented in
Scheme II and involves a series of consecutive pericyclic re-
actions. Herges was able to isolate the intermediates E, and
when subjected to light, these formed a mixture from which
was isolated one specific product. X-ray crystallography
showed that this isomer had the C2 axis of symmetry required
of a Möbius annulene.
This synthesis was set as a problem in an undergraduate
class associated with a course on pericyclic reaction given by
the author, and the students were invited to “push arrows”
illustrating the mechanism, the total number of arrows for
each step then being used to derive which of the 4n
(4n +
2) rules listed above is applicable for that step. One charac-
teristic feature of pericyclic problems is that often, two or
more alternatives to the arrow pushing can be proposed, and
normally these alternatives all result in the same analysis of
the overall reaction step. So although it was no surprise that
the majority of students in the class illustrated step E to F
with the solid arrows (examples of such reactions were con-
tained in the lecture notes for the course), a significant num-
ber of students instead chose to use the dashed arrows for
this step. The stereochemistry at the bicyclic ring junction
in E had been left undefined in the question, in the hope of
provoking the students (and the present author!) to think
about the implications.
A tutorial, in which this problem and possible answers
to it were discussed with students, soon revealed that those
students who had invoked the solid arrows were led to ana-
lyzing the consequences of a 4n + 2 rule (n = 1), while those
who had used the dashed arrows were obliged to use the 4n
rule (n = 3) for this electrocyclic ring-opening reaction. It
1538 Journal of Chemical Education • Vol. 84 No. 9 September 2007
seemed that for either route, one could regard the reaction
as simultaneously following one rule and breaking the other,
and that a contradiction seemed to exist. This certainly led
to a lively tutorial.
[12] Annulene as a Model
Further thought reveals that this specific example can
be used to concisely encapsulate many of the concepts re-
quired to fully understand pericyclic reactions. To illustrate
these, a reasonably accurate quantum mechanical model of
the two possible transition states for this reaction was com-
puted and is analyzed in detail below. Several simplifications
of the system were undertaken to enable a practical model
to be constructed:
1. The size of the annulene was reduced from [16] to [12]
(Scheme III), making it conformationally much less
complex. This exact reaction is actually known, albeit
proceeding in the reverse direction (10).
2. The reaction rate can be increased by either light (as
in Herges’ synthesis) or by heat (9). The theoretical
models were computed for the latter, as exploring the
photochemical potential surface is a far more complex
task, with results that may be expected go well beyond
the conventional Woodward–Hoffmann approach.
3. Also noteworthy is a fascinating article (11) describ-
ing the cis–trans isomerization in the [12] annulene
shown in Scheme III as also involving a Möbius tran-
sition state.
Two transition states were located for the ring opening
reaction. This was done at a level of theory summarized as
B3LYP/6-31G(d), which means use of a density functional
• www.JCE.DivCHED.org

these transition states will be discussed individually:
Scheme III. A simplified model electrocyclic reaction, showing the
plane (Cs ) or axis (C2) of symmetry which can be preserved dur-
ing reaction. Note the either the solid or dashed arrows could be
used to open the ring.
Figure 5. Geometries and transition normal modes for electrocyclic
ring opening shown in Scheme III for transition states with Cs and
with C2 symmetry. The latter shows the same helical features as
previously illustrated in Figure 2. The Supplemental MaterialW con-
tains 3D rotatable models that can be viewed instead (Java must
be installed on your system to enable this).
procedure with an orbital basis set for the atoms known as
6-31G(d). This combination is frequently employed nowa-
days and its properties are well understood.
The first transition state in fact corresponds to the three
solid arrows, maps to the 4n + 2 rule, and hence is deemed
to correspond to a Hückel type in which a plane of symme-
try (Cs) is maintained throughout the reaction. This implies
that the six-membered ring formed by the transition state is
Hückel aromatic (rule 1 above). The second transition state
corresponds to the four dashed arrows, maps to the 4n rule,
and implies that the eight-membered transition ring has C2
symmetry and is Möbius aromatic (rule 5 above). Are these
properties are reflected in the two quantitative measures of
aromaticity described above?
Shown in Figure 5 are 3D models visualized using the
Jmol applet (12) illustrating the calculated geometries of the
two transition states. The model is animated to illustrate the
form of the reaction mode (see the Supplemental MaterialW).
The vibrational mode is computed from a full vibrational
analysis of the system and shows in each case the central C⫺C
bond periodically breaking or making, in one direction lead-
ing to the monocyclic [12] annulene and in the other direc-
tion to the bicyclic starting material. Various properties of
www.JCE.DivCHED.org • Vol. 84 No. 9 September 2007
Research: Science and Education
• The Cs plane and C2 axis of symmetry should be clearly
evident from the two geometries. Each vibrational
mode reflects this symmetry.
• The stereochemistry of each reaction also reflects its
symmetry. The system with Cs has cis stereochemistry
at the bicyclic ring junction, while that with C2 sym-
metry has trans stereochemistry.
• The Cs system is said to have the two termini of the
bond cleaving or forming rotation in opposite direc-
tions, (one clockwise, the other anti-clockwise), a pro-
cess known as disrotation. The C2 system rotates both
termini in the same direction, that is, conrotation.
• The Cs system forms or cleaves the C⫺C bond from
the same face of the π system located on the six-mem-
bered ring, described as suprafacial bond formation–
cleavage. The C2 system forms or cleaves the C⫺C
from the top face of one end of the eight-membered
ring and the bottom face of the other end, described
as antarafacial bond formation–cleavage.
• An even more concise summary of these definitions is
to refer to the transition state with Cs symmetry as hav-
ing Hückel form, and to that with C2 symmetry as
having Möbius form.
• With the Cs system, the C⫺C bond lengths around
the six-membered (putatively aromatic) ring, starting
with the breaking C⫺C bond, are 2.22, 1.425, 1.38,
1.42, 1.38, and 1.425 Å. This pattern shows only a
little deviation from the mean of about 1.40 Å, which
is typical of the length in benzene itself. Omitting the
actual forming or cleaving bond itself, ∆r = 0.04 Å.
Much greater alternation is seen in the values going
around the eight-membered ring: 2.22, 1.46, 1.35,
1.48, 1.34, 1.48, 1.35, and 1.46 (∆r = 0.14 Å) and
these values are more typical of the non-aromatic cyclo-
octatetraene ring. A further feature is that the six-mem-
bered ring is almost planar, while the eight-membered
ring is highly buckled. These geometries clearly indi-
cate that for the Cs isomer, the six-membered ring is
clearly aromatic in accord with the supposition first
suggested above.
• In contrast, the values for the six-membered ring in
the C2 system are 2.37, 1.48, 1.35, 1.47, 1.35 and
1.48, (∆r = 0.13 Å). This alternating pattern is much
reduced for the eight-membered ring: 2.37, 1.38, 1.42,
1.39, 1.43, 1.39, 1.42, and 1.38 (∆r = 0.04 Å). The
former is clearly non-aromatic while the latter is aro-
matic. In addition, the helical nature of the eight-mem-
bered ring can be perceived if compared to that of the
helicene shown in Figure 2.
• The Cs system has a NICS(0) index of ᎑11.1 ppm at
the centroid of the six-membered ring and +0.3 for
the eight-membered ring. Bearing in mind a value of
about ᎑10.0 for benzene, this clearly shows the smaller
ring as the aromatic one.
• The C2 system has a NICS(0) index of +2.5 for the
six-membered ring and ᎑9.5 for the eight-membered
ring, again clearly showing the larger ring now is the
aromatic one.
• Journal of Chemical Education 1539
 Research: Science and Education
These various measures of aromaticity clearly illustrate
how the concept can be applied to transition states for peri-
cyclic reactions. It also enables one to reconcile how a reac-
tion can apparently both follow one rule but break the other
in this hybrid electrocyclic reaction. The answer is that only
one ring is aromatic in each case, while the other ring essen-
tially just spectates as a non-aromatic participant. In effect,
stabilization due to cyclic π conjugation occurs only in the
aromatic ring, while the spectating ring retains conventional
unconjugated bonds.
For those interested in pursuing this topic, an extension
of the reaction in Scheme III to one with two equal-sized
rings is presented in the digital interactive version of this ar-
ticle (see the Supplemental MaterialW).
Conclusions
Chemical reactivity is a complex process, controlled by a
variety of influences. Pericyclic reactions are a class that also of-
ten exhibit highly stereospecific behavior and that are now un-
derstood to be subject to quite clear stereoelectronic influences.
These in turn can be traced back to quite simple derivations of
the Schrödinger wave equation and related to another concept
known as aromaticity. To do so fully, requires an understanding
of selection rules expressed in terms of two different forms of
aromatic species, the ubiquitous planar Hückel aromatic and
the relatively new type of Möbius aromatic. In illustrating the
first synthesis of such a stable Möbius system, we uncover one
step in the sequence where the mechanism can be explained in
terms of either Hückel or of Möbius aromaticity of the transi-
tion state for the reaction. This exposes a very rare example of a
pericyclic reaction that at first sight appears to simultaneously
obey one selection rule and to disobey another. Reconciling this
apparent discrepancy requires a deeper understanding of how
aromaticity as a concept can be applied to such reactions.
WSupplemental
Material
A digital version of this article with interactive figures
is available in this issue of JCE Online.
1540 Journal of Chemical Education • Vol. 84 No. 9 September 2007
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• www.JCE.DivCHED.org