Facile Preparation of 1,5-Diazacyclooctanes from Unsaturated Imines: Effects of the Hydroxyl Groups on [4+4] Dimerization

Abstract

Hydroxyl groups on an unsaturated imine, which may be readily obtained from the corresponding unsaturated aldehyde and the 1,2-ethanolamine derivative, were found to efficiently activate a [4+4] dimerization reaction to produce the eight-membered 1,5-diazacyclooctane. A novel OH–π interaction between the two imines, in addition to the stabilization of the eight-membered diacetals, was proposed based on density functional theory calculations.

Key words

1,5-diazacyclooctanes - unsaturated imines - hydroxyl groups - [4+4] dimerization

• Reference

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