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Divergent mechanisms for the dealkoxycarbonylation of a 2-(3-azetidinyl)malonate by chloride and cyanide

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
21
Identifiers
DOI: 10.1016/s0040-4039(00)73205-9

Abstract

Abstract The reaction of dimethyl 2-(1-benzylazetidin-3-yl)propane-1,3-dioate with NaCN in wet DMSO at high temperature afforded methyl 2-(1-benzylazetidin-3-yl)acetate, whereas similar treatment with NaCl gave methyl 3-benzylazabicyclo-[3.1.0]hexane-2-onecarboxylate. These results provide additional evidence that chloride- and cyanide-mediated cleavages of esters may proceed by different mechanisms.

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