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Vinylic cations from solvolysis. VIII. Solvolysis of cis and trans α-bromo-p,p'-dimethoxystilbenes.

✍ Scribed by Zvi Rappoport; Micha Atidia

Book ID
104249351
Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
232 KB
Volume
11
Category
Article
ISSN
0040-4039

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✦ Synopsis

For the SE1 solvolysis of o(-bromo-p-methoxystyrene 1 2 and of Crisnisylvinyl bromide 2 3 k2/kl = 1.7 in 80,: EtCH. In buffered AcOH k2/kl = 4.2 andz shows an ---extensive bromide ion return, while 1 shows no return. 4 The later difference is attributed to the presenoe of the bulky aryl groups in the ion derived from 2 which are absent in ths ion derived from 1. The study of cis (2) and -@)d-bromo-p,pl-dimethosystilbenes was therefore initiated in order to obtain additional information concerning this point.

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The introduction of two S-substituents into a vinylic system has a relatively small effect on the rate of SN1 solvolysis, 2 while with S-monomethyl a-activated vinyl halides k cis'ktrans values of 8.3 , ' and ~a. 9.5 , 4 vere found. The largest