Synthesis of (+)- and (–)-naphthalene and anthracene 1,2-oxides

Abstract

(–)-Menthyloxyacetyl derivatives of trans-2-bromo-1-hydroxy-1,2,3,4-tetrahydronaphthalene and trans-2 bromo-1-hydroxy-1,2,3,4-tetra hydroanthracene have been synthesized and resolved into diastereoisomers by a combination of short-column chromatography and recrystallization. The chiral oxirans naphthalene 1,2-oxide, anthracene 1,2-oxide,1,2-epoxy- 1,2,3,4-tetrahydronaphthalene, and 1,2-epoxy- 1,2,3,4-tetrahydroanthracene have been obtained in a high state of optical purity. The absolute stereochemistry and optical purity of these epoxides have been determined by several methods including n.m.r. analysis and correlation with alcohols of known configuration.