Download PDF by Paul Fong, ed.: The Arcata Conference on Representations of Finite Groups,
By Paul Fong, ed.
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Extra resources for The Arcata Conference on Representations of Finite Groups, Part I
Reaction of this intermediate with alcohol directly generates a key intermediate, alkoxyphosphonium salt (route A), which undergoes nucleophilic attack by the carboxylate ion to furnish the desired ester. 1 Reaction with Carboxylic Acids alkoxy carbon center in the last SN2 step. An alternative route is possible (route B) [96JOC2967]. After addition of a carboxylic acid to DEAD, an acyloxyphosphonium salt is formed, and this is attacked by an alkoxide ion generated by interaction between an alcohol and the hydrazide ion.
5 mmol, dried well at 140 8C for 3 h in vacuo before use) in acetonitrile is stirred for 1 d at room temperature, and benzyl hexanoate is isolated in 90 % yield after workup and purification. Scheme 1-38 31 32 1 Reaction of Alcohols with Carboxylic Acids and their Derivatives It is claimed that 4,5-dichloro-1,2,3-dithiazolium chloride works at lower temperatures (±78 8C to room temperature) than the 2-halo-1-methylpyridinium chloride (Scheme 1-39) [93TL2737]. 0 mmol) in dry CH2Cl2 (3 mL). The mixture is stirred at ±78 8C for 2 h and allowed to warm to rt overnight (12 h).
Thanks to the neutral conditions, various functional groups are tolerated and, remarkably, otherwise difficult-toachieve transesterification of non-enolizable a,a-disubstituted b-keto esters smoothly takes place.
The Arcata Conference on Representations of Finite Groups, Part I by Paul Fong, ed.