The thermal isomerization of 1‐(α‐aroyloxybenzylideneamino)‐4,5‐di‐methyl‐1,2,3‐triazoles (isoimides) to the corresponding imides | Zendy

Maroulis A. J. | Zendy; HadjiantoniouMaroulis C. P. | Zendy

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The thermal isomerization of 1‐(α‐aroyloxybenzylideneamino)‐4,5‐di‐methyl‐1,2,3‐triazoles (isoimides) to the corresponding imides

Author(s) -

Maroulis A. J.,

HadjiantoniouMaroulis C. P.

Publication year - 1984

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.5570210616

Subject(s) - chemistry , lone pair , nucleophile , moiety , isomerization , nitrogen , medicinal chemistry , sigmatropic reaction , photochemistry , stereochemistry , organic chemistry , catalysis , molecule

The title isoimides rearrange upon heating to the corresponding imides through a [1,3] O⇀N aroyl transfer. The reaction is slightly accelarated by electron withdrawing substituents in the migrating moiety and retarded by electron donating as it is suggested by the positive (+0.5) Hammett ϱ value. The mechanism operating is either a rate determining nucleophilic attack by the nitrogen lone pair on the carbonyl carbon or a sigmatropic [π2s + σ2a] process which does not involve the lone pair of electrons on nitrogen and π or‐bitals of the carbonyl group.

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