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Reductive Scission of a Cyclopropane σ‐Bond During the Action of Elemental Lithium on Cyclopropylacetylenes – A cis ‐1,2‐Dilithioalkene as Intermediate
Author(s) -
Maercker Adalbert,
Girreser Ulrich
Publication year - 1990
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.199006671
Subject(s) - cyclopropane , bond cleavage , chemistry , lithium (medication) , ring (chemistry) , cleavage (geology) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , medicine , fracture (geology) , composite material , endocrinology
The cis ‐dilithioalkene 2 a is stable in solution at −30 °C ; it is formed as intermediate during the reductive cleavage of a cyclopropane bond in 1 a leading to 3 a . In contrast, in the analogous reaction of 1 b , only the product 3b of ring‐opening can be detected, and no intermediate. R = Ph(a), cyclopropyl (b).