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Paper | Regular issue | Vol 41, No. 5, 1995, pp.959-972
Published online, 1st January, 1970
DOI: 10.3987/COM-94-7000
Studies on m-Cyclophane Formation from the Photolysis of Chloroacetamide Derivatives

Robert Rezaie, John B. Bremner*, Gregory K Blanch, Brian W Skelton, and Allan H White

*Department of Chemistry, University of Wollongong, Wollongong, 2522, NSW, Australia

Abstract

The synthesis of 12-hydroxy-2-oxa-6-azabicyclo[7.3.1]trideca-1(13),9,11-trien-5-one (4) is described. Two routes to (4) based on the photolysis of N-[2-(3,4-dimethoxyphenyl)ethyl]chloroacetamide (2b) and N-[2-(4-t-butyldimethylsiloxy-3-methoxyphenyl)ethyl]chloroacetamide (2c) followed by O-demethylation or O-desilylation, were developed. Extension of the work has given the new m-cyclophane ester derivative (9), whose structure has been confirmed by X-ray crystallography.