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Jacs, 1995, 77, 4183 PDF
Jacs, 1995, 77, 4183 PDF
COX~IUNICATIONS
TO THE EDITOR
:lug. 3, 1935
TABLE
I
PRODUCTS
OF REACTION
OF ALLYLIC
ALCOHOLS
WITH THIONYL
CHLORIDE
Alcohol
Reaction conditions
CHKHClCH=CHz
SOCl2,no solvent
CHaCH=CHCHzOH
SOC12, no solvent
CHaCH=CHCHzOH
CHaCHOHCH=CHz
( )transCHsCH=CHCHOHCHa
CsHsCH=CHCHzOH
CsHbCH=CHCH*OH
SOC12 in Et20
SOClz in Et20
Product composition
33% CHaCHClCH=CHs
6770 CH&H=CHCHICl
71% CHoCHClCH=CH*
29 7 0 CH,CH=CCH CHzCl
99% CHsCHClCH=CHt
100% CHsCH=CHCHzCl
100% (-1 tramCHsCH=CHCHClCHs
100% CeHsCHClCH=CHz
60% CsHrCHClCH=CHz
40% CeHsCH=CHCHzCl
SOCl, in EtzO
0.1 M R O H
0.1 MSOCl, in Et20
1 1.l ROH
1 M SOCL in Et20
+
+
FREDERICK
F. CASERIO
GERALDE. DENNIS
DEPARTMENT
OF CHEMISTRY
OF CALIFORNIA
UNIVERSITY
ROBERTH. DEWOLFE
Los ANGELES,CALIFORNIA
WILLIAMG. YOUNG
RECEIVED
APRIL28, 1955
IV
7-Norborneol, m.p. 150-151, was obtained by
catalytic hydrogenation of anfi-7-norbornenol (I).
The first order rate constants (kl)for acetolysis of
the corresponding p-toluenesulfonates in acetic acid
(0.1 M in potassium acetate, containing 1% Ac20),
and other pertinent data, are
I11
,OTs
m.p. 60.5-61.0"
v
ki(205')
AH*
AS*
K1(25')
VI
m.p. 54.7-55.7'
8.40 X
sec.-l
35.7 & 0.6 kcal./mole
-3.5 & 1.7 e.u.
6.36 X 10-'6 sec.-l
4184
C O M h l U N I C A T I O N S TO T H E
EDITOR
Vol. 77
d'--