Role of the gauche effect and local 1,3-dipole-dipole interactions in stabilizing an unusual conformation of tartarodinitriles.

Abstract

This paper reports the synthesis, X-ray and NMR investigations of chiral and meso dinitriles of tartaric acid (tartarodinitriles) and their O,O'-diacetyl and O,O'-dibenzoyl derivatives. While in chiral tartaric acid its esters and NH amides the four-atom carbon chain is overwhelmingly trans, it is gauche in chiral tartarodinitriles. Conversely, meso… (More)
DOI: 10.1107/S0108768108018272

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