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Preparation of β‐hydroxysulfides from 1,2,3‐thiadiazoles. Comparison of the effect of phenylmagnesium bromide on α‐Thio‐ and α‐selenoketones
Author(s) -
Ganjian Iraj
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270735
Subject(s) - chemistry , phenylmagnesium bromide , heteroatom , reagent , bromide , thiadiazoles , thio , medicinal chemistry , nucleophile , organic chemistry , grignard reaction , decomposition , ring (chemistry) , catalysis
Base decomposition of 4‐substituted‐phenyl‐1,2,3‐thiadiazoles at 78° resulted in 2‐(4‐substituted‐phenyl)‐ethynylthiolate anions which were immediately reacted with α‐bromoketones to give a series of α‐(2‐[4‐substituted‐phenyf]ethynyl) thioketones. Unlike the selenophilic reaction of the Grignard reagents with α‐selenoketones, the carbonyl group was the site of nucleophilic attack and the reaction of the α‐thioketones with phenylmagnesium bromide gave the corresponding β‐hydroxysulfides. The difference in mode of action toward the Grignard reagents was attributed to the difference in the bond strengths between carbon and the heteroatoms.