Stereochemical studies of some 1,3-disubstituted phthalans

Abstract

No systematic studies appear to have been reported on the synthesis or methods of assigning the stereochemistry of 1,3-disubstituted phthalans such as 1 - 4. As part of pharmaacological studies (3) on the separated cis-trans isomers of 1-(N,N-dimethylaminomethyl)-3-phenylphthalan (3) prepared sequentially from 1 and 2 it was desirable to establish the stereochemical configurations of the cis-trans isomers of 1-4. We report here nonstereospecific syntheses of 1-4, proton and ^(13)C nmr studies which are somewhat indicative of the configurations, stereoselective syntheses of the cis isomers of 2 - 4 from o-benzoylbenzaldehyde and confirmation of the nmr assignments by X-ray diffraction determination of the crystal structure of trans-1.

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