The Journal of Organic Chemistry

Cyclization of phenyl azides with homoallylic or allylic ortho substituents and the consequences of triazoline fragmentation

PAS Smith, SSP Chou

Index: Smith, Peter A. S.; Chou, Shang-shing Peter Journal of Organic Chemistry, 1981 , vol. 46, # 20 p. 3970 - 3977

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Citation Number: 32

Abstract

o-(A1lyloxy) phenyl azide (1) and 14 derivatives substituted on the allyl group were thermolyzed at 110-120" C to form benzoxazines (16), dihydroazirinobenzoxazines (17), or 3-alkenylbenzomorpholines (18, 19) through fragmentation of intermediate triazoliies. With substituted allyl groups, the geometrical isomers gave the same products in the same ratio, except in the case of o-(fi, r-dimethylallyl) phenyl azide. Rearrangement by phenyl ...