Anodic Grob Fragmentation of Bicycloalkylcarboxyl Acids to Specifically Disubstituted Cycloalkenes | Zendy

Michaelis Ralf | Zendy; Müller Ulrich | Zendy; Schäfer Hans J. | Zendy

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Anodic Grob Fragmentation of Bicycloalkylcarboxyl Acids to Specifically Disubstituted Cycloalkenes

Author(s) -

Michaelis Ralf,

Müller Ulrich,

Schäfer Hans J.

Publication year - 1987

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198710261

Subject(s) - cyclopentanes , chemistry , electrolysis , fragmentation (computing) , anode , medicinal chemistry , organic chemistry , stereochemistry , biology , catalysis , ecology , electrode , electrolyte

3,4‐Disubstituted cyclopentenes 2 are formed stereospecifically in the non‐Kolbe electrolysis of lactonized 3‐substituted 6‐hydroxy‐2‐norbornanecar‐boxylic acids 1 , trans ‐ 2 is obtained from exo ‐ 1 and cis ‐ 2 from endo ‐ 1 . Cyclohexenes, cyclopentanes, and acyclic compounds can be prepared in this way from suitably chosen starting materials. R CO 2 t Bu, SO 2 Ph (selected).

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