Premium
Synthese mittlerer und großer Ringe, XXXVI. Synthese eines überbrückten, in‐konfigurierten Bicyclo[2.1.0]pentan‐Derivates
Author(s) -
Tochtermann Werner,
Sdunnus Norbert,
Wolff Christian,
Reggelin Michael
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270714
Subject(s) - chemistry , bicyclic molecule , sodium methoxide , allylic rearrangement , halogenation , stereochemistry , deoxygenation , derivative (finance) , stereoselectivity , medicinal chemistry , organic chemistry , methanol , financial economics , economics , catalysis
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.