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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).