Dibenzo[<i>a</i>,<i>d</i>]cycloheptene and related compounds. II. The synthesis of some 11-substituted dibenzo[<i>b</i>,<i>e</i>]azepin-6-one, 5-substituted dibenzo[<i>a</i>,<i>d</i>]cycloheptene, and 12-substituted dibenzo[<i>a</i>,<i>d</i>]cyclooctene derivatives

Abstract

The synthesis of several 11-substituted-5,6-dihydro-11H-dibenzo[b,e]azepin-6-ones, and an improved method of preparing 5-cyano-10,11-dihydro-5H-dibenzo[a,d]cycloheptene and 12-cyano-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene are described.A description of the synthesis of epoxides from diaryl ketones and dimethylsulfonium methylide by a modified technique is given.The nuclear magnetic resonance spectra of several of the 11-substituted dibenzo[b,e]azepin-6-ones are interpreted on the basis of a slow interconversion between diastereomeric boat conformers in which the C-11 substituent is quasi axial or quasi equatorial.