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Thiophene Derivatives by Novel Rearrangements of Siloxy‐substituted Cyclopropanecarboxylates
Author(s) -
Brückner Christiane,
Reissig HansUlrich
Publication year - 1985
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.198505881
Subject(s) - thiophene , chemistry , medicinal chemistry , ring (chemistry) , alkyl , iodide , derivative (finance) , methyl iodide , lewis acids and bases , organic chemistry , catalysis , financial economics , economics
The ester enolate of the siloxycyclopropanecarboxylate 1 reacts with CS 2 and methyl iodide to give a ring‐expanded dihydrothiophene derivative, which, via Lewis acid‐induced shifting of an alkyl group, gives the thiophene 2 . The reaction can be extended to analogues of 1 ; the OSi(CH 3 ) 3 group, however, is indispensable.