THE SYNTHESIS, PHYSICAL, AND SPECTRAL PROPERTIES, AND SOME REACTIONS OF A NEW STABLE bis-α-LACTAM (AZIRIDINONE) WITH A TERPENE SKELETON

Abstract

A synthesis of a new stable bis-α-lactam, cis-1,1′(p-menth-1,8-ylene) bis(3-tert-butyl-2-azirididone) (4), derived from p-menthane, is described. Complete spontaneous thermal decomposition required 1h of reflux in boiling n-decane (b.p. 174°C) and the products are 2,2-dimethylpropanal (pivalaldehyde) (6) and 1,8-diisocyano-p-menthane (7). Reaction with benzylamine yielded the unexpected bis-benzylamide (13a), while reaction with sodium methoxide gave the bis-α-amino acid ester (14).

ACKNOWLEDGMENT

We thank Professor Klaus Biemann, Department of Chemistry, Massachusetts Institute of Technology, for the high resolution mass spectra.