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- Title
Synthèse et réactions de didésoxy-5,6-halogéno-6-α-D- xylo-hepténo-5-furannurononitriles. Communication préliminaire.
- Authors
Tronchet, Jean M. J.; Martin, Olivier R.
- Abstract
Synthesis and reactions of 5,6-dideoxy-6-halogeno-α-D- xylo-hept-5-eno-furanurononitriles The 5,6-dideoxy-6-chloro-, 6-iodo- and 6-fluoro-3- O-methyl-α- D- xylo-hept-5-eno-furanurononitriles have been prepared, their properties described as well as the methods used for the assignment of the configuration of the geometrical isomers. Some new reactions of the 6-bromo analog ( 1) of these compounds are reported. For example, when reacted with 2-mercaptoethanol or N, N′-dimethyl-ethylenediamine in the presence of NaOH, 1 gave the corresponding six-membered ring, stereo-isomers of an oxathiane or of a perhydrodiazine respectively. When the base used was Et3N and the binucleophile the N-methyl-ethanolamine or the N, N′-dimethyl-ethylene-diamine the major product was a cyano-enamine which could be hydrolysed to a β-cyanoketone or cyclized to a five-membered ring, an oxazolidine or an imidazolidine respectively.
- Publication
Helvetica Chimica Acta, 1977, Vol 60, Issue 2, p585
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19770600231