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New Facts on the Stereoselectivity of Monobromocarbenoid Additions to Cyclic Alkenes

โœ Scribed by Dehmlow, Eckehard V. ;Lustinetz, Horst

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
308 KB
Volume
1996
Category
Article
ISSN
0947-3440

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โœฆ Synopsis

Abstract

The monobromocarbenoid derived from CH~2~Br~2~ and NaN(SiMe~3~)~2~ gives only endo adducts 4, 5, and 6 with 1,5โ€cyclooctadiene, but shows no selectivity with 1,3โ€cyclooctadiene. A literature report of a high endo adduct preference of cyclooctene cannot be duplicated, but cyclodecene is converted to 3 with 100% selectivity. Bromocarbenoid adducts 11, 13, and 14 of norbornene and norbornadiene are reported. A possible explanation for the varying selectivities is given.

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