CONCAVE REAGENTS .20. STERICALLY SHIELDED M-TERPHENYLS AS SELECTIVE AGENTS IN GENERAL PROTONATIONS

Authors
LUNING U BAUMGARTNER H MANTHEY C MEYNHARDT B
Citation
U. Luning et al., CONCAVE REAGENTS .20. STERICALLY SHIELDED M-TERPHENYLS AS SELECTIVE AGENTS IN GENERAL PROTONATIONS, Journal of organic chemistry, 61(22), 1996, pp. 7922-7926
Citations number
52
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
22
Year of publication
1996
Pages
7922 - 7926
Database
ISI
SICI code
0022-3263(1996)61:22<7922:CR.SSM>2.0.ZU;2-3
Abstract
New m-terphenyls with acidic substituents in the 2'-position have been used in general protonations leading to reagent-controlled selectivit y enhancements: up to 96:4 for the gamma/alpha-protonation of unsymmet rically substituted allyl anions, up to 97:3 for the protonation of cy clohexyl anions generating preferentially the thermodynamically less s table cis-products. In order to allow a general, reagent-controlled pr otonation the acidity of the protonating agent should be as low as pos sible.