FORMATION OF CARBON-CARBON BONDS VIA QUINONE METHIDE-INITIATED CYCLIZATION REACTIONS

Authors
ANGLE SR ARNAIZ DO BOYCE JP FRUTOS RP LOUIE MS MATTSONARNAIZ HL RAINIER JD TURNBULL KD YANG WJ
Citation
Sr. Angle et al., FORMATION OF CARBON-CARBON BONDS VIA QUINONE METHIDE-INITIATED CYCLIZATION REACTIONS, Journal of organic chemistry, 59(21), 1994, pp. 6322-6337
Citations number
71
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
21
Year of publication
1994
Pages
6322 - 6337
Database
ISI
SICI code
0022-3263(1994)59:21<6322:FOCBVQ>2.0.ZU;2-8
Abstract
p-Quinone methides were found to be excellent electrophilic cyclizatio n initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2, 6-disubstituted phenols with Ag2O afforded the corresponding quinone m ethides. A wide range of cyclization terminators/nucleophiles were fou nd to be effective in the cyclizations, including: allylsilane, beta-k eto esters, furan, pyrrole, indole, and a number of alkenes. The yield s of the cyclizations were generally high.