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Mechanisms of acylation of 2,3‐dihydrobenzoxazol‐2‐one and 2 H ‐1,4‐benzoxazin‐3(4 H )‐one
Author(s) -
Cotelle Nicole,
Cotelle Philippe,
Capelle Sylvie,
Lesieur Daniel
Publication year - 1990
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.610031207
Subject(s) - acylation , chemistry , derivative (finance) , kinetics , medicinal chemistry , organic chemistry , stereochemistry , catalysis , physics , quantum mechanics , financial economics , economics
The kinetics of the acylation of 2,3‐dihydrobenzoxazol‐2‐one with dodecanoic acid in polyphosphoric acid were investigated. Two competitive reactions occurred at the 3‐ and 6‐positions. The acylation reactions in polyphosphoric acid of 2,3‐dihydrobenzoxazol‐2‐one and 2 H ‐1,4‐benzoxazin‐3(4 H )‐one give 6‐ and 7‐acyl derivatives. 4‐Acetyl‐2 H ‐1,4‐benzoxazin‐3(4 H )‐one rearranged in polyphosphoric acid exclusively to the 7‐acetyl derivative. Two mechanisms are proposed to explain the different reaction sites for the acylation of 2 H ‐1,4‐benzoxazin‐3(4 H )‐one.