Nitroalkene

From Wikipedia, the free encyclopedia

Jump to navigationJump to search
A nitroalkene, or nitro olefin, is a functional group combining the functionality of its
constituent parts, an alkene and nitro group, while displaying its own chemical
properties through alkene activation, making the functional group useful in specialty
reactions such as the Michael reaction or Diels-Alder additions.[1]

Synthesis[edit]
Nitroalkenes are synthesized by various means, notable examples include:

 Nitroaldol reactions such as the Henry reaction:[1][2][3][4]

 Nitration of an alkene with nitryl iodide

generated in-situ from silver nitrite and
elemental iodine:[5]

 Direct nitration of alkenes with nitric oxide and

an aluminum oxide catalyst in acidic conditions:[6]

 Direct nitration of alkenes with Clayfen (Iron(III)

nitrate supported on Montmorillonite clay):[7]
  Dehydration of nitro-alcohols:[8]

Reactions[edit]
Nitroalkenes are useful intermediates for various chemical
functionalities.

 A nitroalkene behaving as a Michael acceptor in

the synthesis of Lycoricidine:[1][9]

 Nitroalkene acting as an
activated dienophile toward butadiene in a Diels-
Alder cycloaddition:[1][10]

 The synthesis of pyrrole derivatives via

the Barton–Zard reaction:[11]
  Pericyclic reaction of a nitroalkene yielding
an indole:[12]

 Partial hydrogenation to an alkene baring

a hydroxylamine functional group:[13]

 Reduction to primary amines:[13][14]

 Asymmetric Stetter reaction:[15]

References[edit]
1. ^ Jump up to:        Furniss, Brian; Hannaford, Antony; Smith,
a b c d

Peter & Tatchell, Austin (1996).  Vogel's Textbook of

Practical Organic Chemistry 5th Ed. London: Longman
 Science & Technical. pp. 635, 768, 1035–1036, &
1121.  ISBN  9780582462366.
2. ^ Ballini, Roberto; Castagnani, Roberto; Petrini, Marino
(1992). "Chemoselective synthesis of functionalized
conjugated nitroalkenes". The Journal of Organic
Chemistry.  57  (7): 2160–
2162.  doi:10.1021/jo00033a045.
3. ^ Worrall, David E. (1929). "Nitrostyrene". Org. Synth. 9:
66.  doi:10.15227/orgsyn.009.0066.
4. ^ Chandrasekhar, S.; Shrinidhi, A. (2014). "Useful
Extensions of the Henry Reaction: Expeditious Routes to
Nitroalkanes and Nitroalkenes in Aqueous
Media".  Synthetic Communications. 44 (20): 3008–
3018.  doi:10.1080/00397911.2014.926373.  S2CID 9843
9096.
5. ^ Waldman, Steve; Monte, Aaron, Monte; Bracey, Ann &
Nichols, David (1996). "One-pot Claisen
rearrangement/O-methylation/alkene isomerization in the
synthesis of ortho-methoxylated
phenylisopropylamines". Tetrahedron Letters.  37  (44):
7889–7892.  doi:10.1016/0040-4039(96)01807-2.
6. ^ Mukaiyama, T.; Hata E. & Yamada, T. (1995).
"Convenient and Simple Preparation of Nitroolefins
Nitration of Olefins with Nitric Oxide". Chemistry
Letters.  24  (7): 505–506.  doi:10.1246/cl.1995.505.
7. ^ Varma, Rajender; Naicker, Kannan; Liesen, Per
(1998). "Selective nitration of styrenes with clayfen and
clayan: A solvent-free synthesis of β-
nitrostyrenes".  Tetrahedron Letters. 39 (23): 3977–
3980.  doi:10.1016/S0040-4039(98)00740-0.
8. ^ Ranganathan, Darshan; Rao, Bhushan; Ranganathan,
Subramania; Mehrotra, Ashok & Iyengar, Radha (1980).
"Nitroethylene: a stable, clean, and reactive agent for
organic synthesis".  The Journal of Organic
Chemistry.  45  (7): 1185–
1189.  doi:10.1021/jo01295a003.
9. ^ Jubert, Carole & Knochel, Paul (1992). "Preparation of
polyfunctional nitro olefins and nitroalkanes using the
copper-zinc reagents RCu(CN)ZnI". The Journal of
Organic Chemistry.  57  (20): 5431–
5438.  doi:10.1021/jo00046a027.
10. ^ Noboru Ono; Hideyoshi Miyake; Akio Kamimura &
Aritsune, Kaji (1987). "Regioselective Diels–Alder
reactions. The nitro group as a regiochemical control
element".  Perkin Transactions. 1: 1929–
1935.  doi:10.1039/P19870001929.
11. ^ Jie Jack Li (2013).  Heterocyclic Chemistry in Drug
Discovery. New York:
Wiley. ISBN 9781118354421. pp.43-4
12. ^ Novellino, Luisa; d'Ischia, Marco & Prota, Giuseppe
(1999). "Expedient Synthesis of 5,6-Dihydroxyindole and
Derivatives via an Improved Zn(II)-Assisted 2,β-
Dinitrostyrene Approach". Synthesis. 1999 (5): 793–
796.  doi:10.1055/s-1999-3469.
 13. ^ Jump up to:    Masahiko Kohno; Shigehiro Sasao & Shun-
a b

Ichi Murahashi (1990). "Synthesis of Phenethylamines by

Hydrogenation of β-Nitrostyrenes".  Bulletin of the
Chemical Society of Japan.  63  (4): 1252–
1254.  doi:10.1246/bcsj.63.1252.
14. ^ Koch, Werner & Reichert, Benno (1935). "Über die
katalytische Hydrierung substituierter ω-
Nitrostyrole". Archiv der Pharmazie. 273 (18–20): 265–
274.  doi:10.1002/ardp.19352731802.  S2CID 95731916.
15. ^ DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T.
(2009).  "Catalytic Asymmetric Intermolecular Stetter
Reaction of Heterocyclic Aldehydes with Nitroalkenes:
Backbone Fluorination Improves Selectivity". Journal of
the American Chemical Society. 131 (31): 10872–
10874. doi:10.1021/ja904375q. PMC  2747345.  PMID  19
722669.

Categories: 
 Alkene derivatives
 Nitro compounds
 Functional groups
Navigation menu
 Not logged in
 Talk
 Contributions
 Create account
 Log in
 Article
 Talk
 Read
 Edit
 View history
Search
Search Go

 Main page
 Contents
 Current events
 Random article
 About Wikipedia
 Contact us
 Donate
Contribute
 Help
 Learn to edit
 Community portal
 Recent changes
  Upload file
Tools
 What links here
 Related changes
 Special pages
 Permanent link
 Page information
 Cite this page
 Wikidata item
Print/export
 Download as PDF
 Printable version
Languages
 Deutsch
 ‫فارسی‬
 Polski
 Português
 தமிழ்
Edit links
 This page was last edited on 8 February 2021, at 09:03 (UTC).
 Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By
using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of
the Wikimedia Foundation, Inc., a non-profit organization.
 Privacy policy

 About Wikipedia

 Disclaimers

 Contact Wikipedia

 Mobile view

 Developers

 Statistics

 Cookie statement