Aspects of stereochemistry. Part XXIV. The acid-catalysed rearrangement of 2,4-O-benzylidene-D-erythrose and 2,3-O-benzylidene-erythritol

Autor:	A. B. Foster, K. W. Buck, B. H. Rees, N. Baggett, J. M. Webber
Rok vydání:	1966
Předmět:	chemistry.chemical_compound Stereospecificity chemistry Stereochemistry Erythrose Organic Chemistry Dimethylformamide Phenyl group Erythritol
Zdroj:	Journal of the Chemical Society C: Organic. :212
ISSN:	0022-4952
DOI:	10.1039/j39660000212
Popis:	On treatment with toluene-p-sulphonic acid in dimethylformamide, 2,4-O-benzylidene-D-erythrose rearranges to 2,3-O-benzylidene-D-erythrofuranose with the phenyl group endo. The structure assigned to the rearranged product is proved, and a mechanism is presented which accounts for the stereospecificity. Under similar acid conditions, “cis”-2,3-O-benzylidene-erythritol rearranges into 1,3-O-benzylidene-DL-erythritol.
Databáze:	OpenAIRE
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