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
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
SYNTHETIC APPLICATIONS
MALONATE ESTERS
BETA-KETO-ESTERS
DIPOLAR APROTIC MEDIA
Methyl sulfoxide
Four membered ring
Nitrogen heterocycle
Azetidine derivatives
Decarbalkoxylation
Bicyclic compound
Ketoester
Sodium Cyanides
Sodium Chlorides
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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