Synthese mittlerer und großer Ringe, XXXVI. Synthese eines überbrückten, in‐konfigurierten Bicyclo[2.1.0]pentan‐Derivates | Zendy

Tochtermann Werner | Zendy; Sdunnus Norbert | Zendy; Wolff Christian | Zendy; Reggelin Michael | Zendy

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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.

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