diexo- and diendo-3-hydroxymethylbicyclo[2.2.1]hept-2-yl- and hept-5-en-2-yl-amines (1)-(4) and their N-methyl and N-benzyl derivatives with phenyl isothiocyanate furnished via thioureas (5)-(8) the condensed skeleton tricyclic 2-phenylimino-1,3-thiazines (9)-(12) and 1,3-oxazine-2-thiones (13) and (14) as by-products in acidic medium. By base-catalysed cyclization of the isothiuronium salts of (5)-(8), the 2-phenylimino-1,3-oxazines (15)-(18) were obtained. The complete series of structural and annelation isomers of the norbornanes-norbornenes and oxazines-thiazines permitted a systematic 1H and 13C n.m.r. spectroscopic study of the correlation between the spectral parameters and the structural features in this family of compounds.
|Number of pages||7|
|Journal||Journal of the Chemical Society, Perkin Transactions 2|
|Publication status||Published - Jan 1 1987|
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