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1‐Chloro‐2,2‐bis(4‐chlorophenyl)‐1‐lithioethene · TMEDA · 2THF: Structure of a LiCl Carbenoid
Author(s) -
Boche Gernot,
Marsch Michael,
Müller Achim,
Harms Klaus
Publication year - 1993
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.199310321
Subject(s) - carbenoid , substituent , chemistry , crystal structure , nucleophile , stereochemistry , medicinal chemistry , atom (system on chip) , trigonal crystal system , catalysis , crystallography , rhodium , organic chemistry , computer science , embedded system
The ClCl bond in the carbenoid 1 is about 12 pm longer than that in the compound containing a H atom in place of the Li substituent. This explains the facile reaction of carbenoids with the nucleophiles RLi. The X‐ray crystal structure of 1 is consistent with 13 C‐NMR data, as well as with the stereochemistry of reactions of carbenoids with RLi or the Fritsch–Buttenberg–Wiechell rearrangement of vinyl carbenoids.