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Trapping of 4‐Halo‐2‐chlorobicyclo[2.1.1]hex‐1‐ene: DFT Calculations on This and Related Molecules
Author(s) -
Ströter Thomas,
Jarosch Oliver,
Szeimies Günter
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990503)5:5<1422::aid-chem1422>3.0.co;2-e
Subject(s) - ene reaction , cyclopentene , hypersurface , carbene , trapping , chemistry , molecule , halo , olefin fiber , computational chemistry , stereochemistry , catalysis , physics , organic chemistry , mathematics , mathematical analysis , ecology , quantum mechanics , galaxy , biology
One of the most highly strained bridghead alkenes —bridgehead olefin A , a trans cyclopentene analogue—has been trapped by MeLi and, in an ene reaction, by α ‐methylstyrene. DFT calculations have shown that A is a local minimum on the corresponding energy hypersurface, but that rearrangement of A to carbene B (X = Cl) needs an energy barrier of only 8.4 kcal mol −1 .