ChemInform Abstract: Oxidative Photoaddition of N‐Nitrosodimethylamine to 1‐Phenylpropenes.

Abstract

144ChemInform Abstract In the presence of HCl and under oxygen purging, the nitrosamine (V) photolytically adds to the arylpropenes (Ia), (Ic) to give threo-and erythro-α-amino nitrates (III) or (VIII) as the primary products which are reduced to yield the α-amino alcohols (IV) or (IX), respectively. The compounds (II) or (VII) are formed as by-products in the photoreaction. The analogue (VI) of (II) is formed from (Ib). -The mechanism and stereochemical course of the addition as well as the solvolysis of the diastereomeric α-amino nitrates (III), (VIII) are discussed in detail.