α‐Versus β‐carbon nucleophilic attack in vinylic substitution | Zendy

Shainyan B. A. | Zendy

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α‐Versus β‐carbon nucleophilic attack in vinylic substitution

Author(s) -

Shainyan B. A.

Publication year - 1993

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.610060110

Subject(s) - chemistry , intramolecular force , bromine , nucleophilic substitution , substitution (logic) , carbon atom , carbon fibers , medicinal chemistry , substitution reaction , nucleophile , stereochemistry , organic chemistry , ring (chemistry) , catalysis , materials science , composite number , computer science , composite material , programming language

The mechanism of substitution of the bromine atom in ( Z )‐α‐bromo‐β‐arylthiovinyl phenyl sulphones, PhSO 2 CBr = CHSAr, with arylthiolates, Ar′S − was studied. The same mixture of the four possible products, PhSO 2 C(SAr′) = CHSAr (Ar, Ar′ = p ‐Tol, p ‐CIC 6 H 4 ), was formed in both cross‐experiments (Ar ≠ Ar′). A mechanism involving 1,2‐intramolecular migration of the arylthio group is suggested.

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