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In situ alcohol oxidation-Wittig reactions

✍ Scribed by Xudong Wei; Richard J.K Taylor

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
201 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Allylic, propargylic and benzylic alcohols can be oxidised with activated manganese dioxide in the presence of stabilised Wittig reagents to generate ~t,13-unsatnrated esters directly. This simple procedure, which can also be utilised with diols to give double homologation, is generally useful and particularly valuable ff the intermediate aldehydes are difficult to isolate, toxic or prone to isomerisation.

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In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid
✍ Leonie Blackburn; Hisashi Kanno; Richard J.K. Taylor πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 313 KB

Benzylic, allylic, propargylic and unactivated alcohols can be oxidised with activated manganese dioxide in the presence of N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide to generate directly the corresponding a,b-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides is