STRUCTURES OF SATURATED AZETO[1,2-A][3,1]BENZOXAZINE AND AZETO-[2,1-B][1,3]BENZOXAZINE PREPARED BY ADDITION OF CHLOROACETYL CHLORIDES TOCYCLOHEXANE-CONDENSED DIHYDROOXAZINES

Saturated cis and trans 3,1- and 1,3-benzoxazines (1-4) reacted with c hloroacetyl chlorides to yield azeto[1,2-a][3,1]- and [2,1-b][1,3]benz oxazines (5, 6, 8, 9a,b). In one case, the addition took place with pa rtial cis-->trans inversion of the starting compound. Adduct (7), cont aining two condensed 1,3-oxazine rings, was also isolated. The stereos tructures of the new compounds were proved by H-1 and C-13-nmr spectro scopy, with NOE measurement data. The reaction mechanism is discussed.