Acylation of aromatic substrates with ketenes. An example of vinyl oxocation reactivity
KR Fountain, P Heinze, M Sherwood…
Index: Fountain, K.R.; Heinze, Pamela; Sherwood, Mark; Maddex, Dave; Gerhardt, Greg Canadian Journal of Chemistry, 1980 , vol. 58, p. 1198 - 1205
Full Text: HTML
Citation Number: 5
Abstract
Acylations of aromatic substrates with ketenes involve the reactivity of species similar to vinyl cations. Resonance stabilization of ketene-aluminum chloride complexes seems to make these complexes less reactive than corresponding vinyl cations. The kinetic isotope effect of the reaction with dimethylketene and benzene is 1.06, compatible with vinylcation cases, but not with acylation with CH3COBF4 types of electrophiles. Substrate specificity was ...
Related Articles:
A base-promoted deprotection of 1, 3-dioxolanes to ketones
[Yuan, Changchun; Yang, Li; Yue, Guizhou; Yu, Tianzi; Zhong, Weiming; Liu, Bo Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6972 - 6976]
[Hachiya, Iwao; Moriwaki, Mitsuhiro; Kobayashi, Shu Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 7 p. 2053 - 2060]
[Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko Tetrahedron Letters, 2011 , vol. 52, # 18 p. 2344 - 2347]
[Jean, Mickael; Renaulty, Jacques; Uriac, Philippe; Capet, Marc; Van De Weghe, Pierre Organic Letters, 2007 , vol. 9, # 18 p. 3623 - 3625]
DMF as Carbon Source: Rh-Catalyzed α-Methylation of Ketones
[Li, Yang; Xue, Dong; Lu, Wei; Wang, Chao; Liu, Zhao-Tie; Xiao, Jianliang Organic Letters, 2014 , vol. 16, # 1 p. 66 - 69]