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Paper | Special issue | Vol 40, No. 1, 1995, pp.349-355
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S41
Steric Configuration and Reactivity of 2-Benzylidene-4-methyl-2H-1,4-bensoxazin-3(4H)-one

Piero Dalla Croce, Raffaella Ferraccioli, and Concetta La Rosa

*Dipartimento di Chimica Organica e Industriale, Centro C. N. R., V. Venezian 21 I-20133 Milano, Italy


The reactivity of 2-benzylidene-4-methyl-2H-1,4-benzoxazin-3(4H)-one (1) towards N- and C-nucleophiles, nucleophilic and electrophilic alkenes, dienes and 1,3-dipoles was investigated. Nitrones (2) reacted with 1 giving through a regioselective process a mixture of the two diastereoisomeric spiro compounds (3) and (4) whose structure and relative steric configuration have been assigned on the basis of 1H and 13C nmr data.