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

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 evidenc...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 21; pp. 3441 - 3444
Main Authors Gilligan, Paul J., Krenitsky, Paul J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.05.1994
Elsevier
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Summary: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. Dealkoxycarbonylation of dimethyl 2-(1-benzylazetidin-3-yl)propane-1,3-dioate with NaCN or NaCl in wet DMSO afforded different products.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)73205-9