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New Facts on the Stereoselectivity of Monobromocarbenoid Additions to Cyclic Alkenes
Author(s) -
Dehmlow Eckehard V.,
Lustinetz Horst
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961217
Subject(s) - chemistry , norbornadiene , selectivity , cyclooctene , adduct , norbornene , stereoselectivity , bridged compounds , 1,5 cyclooctadiene , medicinal chemistry , stereochemistry , organic chemistry , polymerization , catalysis , polymer
Abstract The monobromocarbenoid derived from CH 2 Br 2 and NaN(SiMe 3 ) 2 gives only endo adducts 4, 5 , and 6 with 1,5‐cyclooctadiene, but shows no selectivity with 1,3‐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.