Oxidative photoaddition of N‐nitrosodimethylamine to 1‐phenylpropenes

Abstract

Yuan L . Chow et al. / Oxidative photoaddition of N-nitrosodimethylamine to 1 -phenylphropenes Red. Trav. Chim. Pays-Bas 105, 312-316 (1986) 0 165-05 13/86/093 12-05 S I .75 Abstract. In the presence of hydrochloric acid and under oxygen purging, N-nitrosodimethylamine photolytically adds to 1 -arylpropenes regiospecifically to give erythro-and threo-a-amino nitrates as the primary products which can then be reduced, using lithium aluminium hydride, to give a-amino alcohols or can undergo substitution reactions under photochemical conditions. The stereochemical courses of the addition, as well as the solvolysis of the diastereoisomeric a-amino nitrates with intramolecular amino group participation, are discussed in order to explain the product distributions.