In:
European Journal of Organic Chemistry, Wiley, Vol. 2007, No. 6 ( 2007-02), p. 953-958
Abstract:
Cycloalkenes proceed through bromination, dehydrobromination and dibromocarbene addition reactions to give tribromocyclopropanes 10 and 11 . The treatment of tribromocyclopropanes 10 and 11 with 3 equiv. of methyllithium in diethyl ether at –78 °C followed by treatment with trimethylsilyl chloride produce 8‐(trimethylsilyl)bicyclo[5.1.0]oct‐1(8)‐ene ( 4 ) and 9‐(trimethylsilyl)bicyclo[6.1.0]non‐1(9)‐ene ( 5 ). Both 4 and 5 undergo ene dimerization via the same steric isomer and an endo transition state to generate the stable adducts 6 and 7 , respectively, as the sole isomers. Compound 6 , containing an unstable bicyclo[5.1.0]oct‐1(8)‐enyl group and produced in high yields, has been reported to be an unstable species. Both of the ene dimers, (trimethylsilyl)cyclopropenes 6 and 7 , can be converted into cyclopropenes 8 and 9 by treatment with a fluoride salt followed by protonation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2007:6
DOI:
10.1002/ejoc.200600771
Language:
English
Publisher:
Wiley
Publication Date:
2007
detail.hit.zdb_id:
1475010-7
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