Premium
The chlorinalion of 3,5‐dimethyl‐1,2,4‐oxadiazole
Author(s) -
Burden John A.,
Heywood Donald L.
Publication year - 1972
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.5570090625
Subject(s) - chemistry , oxadiazole , reactivity (psychology) , toluene , medicinal chemistry , organic chemistry , polymer chemistry , photochemistry , medicine , alternative medicine , pathology
The clilorination of 3,5‐dimethyl‐1,2,4‐oxadiazole has been studied using both photo and thermal initiation. It has been found that photoinitiation allows reaction at both the 3‐ and 5‐methyl group, the former being preferred by a factor of 3‐4 at moderate (up to 75° ) temperature. The difference in reactivity is related to a difference in electron availability at the two reaction sites. The thermally initiated chlorination occurs almost exclusively at the 5‐methyl group. Overall, 3,5‐dimethyl oxadiazole is much less active than toluene or cyclo‐liexane toward chlorination.