W. Tochtermann, Norbert Sdunnus, C. Wolff
Jul 1, 1994
Citations
0
Influential Citations
2
Citations
Journal
Chemische Berichte
Abstract
Synthesis of Medium and Large Rings, XXXVI. — Synthesis of a Bridged Bicyclo[2.1.0]pentane Derivative with inside Configuration Dihydrocyclobutafurans 4 (H instead of Br) are reactive intermediates in the photochemical rearrangement of 3,6-hexanooxepine-4,5-dicarboxylic esters. The synthesis of the bromo derivative 4 was achieved by irradiation of the epoxyoxepine 1 followed by a regio- and stereoselective NBS bromination of 2 and deoxygenation of 3 with tungsten hexachloride/n-butyllithium. Treatment of the allylic bromide 4 with sodium methoxide gave surprisingly the title compound 5. The structure of 5 was established by thorough NMR analysis.