M. Wada, H. Konishi, Katsuhiko Kirishima
Nov 15, 1997
Citations
0
Influential Citations
15
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
2,4,6-Trimethoxyphenyllithium, Φ′Li[Φ′ = 2,4,6-(MeO)3C6H2], reacted with diphenyl carbonate and with ethyl formate to give tris(2,4,6-trimethoxyphenyl)methanol, Φ′3COH (1), and bis(2,4,6-trimethoxyphenyl)methanol, Φ′2CHOH (2), respectively. Compound 1 reacted with a slight excess of perchloric acid in 2-propanol to give very dark-purple crystals of the triarylcarbenium salt, [Φ′3C]X (3, X = ClO4), which were inert even in hot ethanol. However, a treatment of 3 (X = Cl), prepared in situ in 1 M (1 M = 1 mol dm−3) hydrochloric acid, with 1 M sodium hydroxide resulted to give 4-bis(2,4,6-trimethoxyphenyl)methylene-3,5-dimethoxy-2,5-cyclohexadienone. Compound 2 also reacted with a slight excess of perchloric acid in methanol to give dark-red crystals of the diarylcarbenium salt, [Φ′2CH]X (5, X = ClO4). Compound 5 was considerably inert even in hot methanol, but was easily reduced in primary and secondary alcohols to give bis(2,4,6-trimethoxyphenyl)methane, Φ′2CH2. Measurements of the half-lives of 5 in these ...