Ring-Expansion Reactions of Epoxy Amides and Enamides: Functionalized Azetidines, Dihydrofurans, Diazocanes, or Dioxa-3-azabicyclonon-4-enes?

Functionalized azetidines, 2,3-dihydrofurans, or the unorthodox dioxa-3-azabicyclonone-4-ene motifs are the products from transition metal-free reaction between N-oxiranylmethyl benzenesulfonamide and beta-chloro-cinnamaldehyde, depending on whether one uses either NaI/K2CO3 or LiBr/K2CO3. These rin...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 87; no. 10; pp. 6612 - 6629
Main Authors: Suraj, Swamy, K. C. Kumara
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 20.05.2022
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
SULFONAMIDES
YNAMIDES
DERIVATIVES
BUILDING-BLOCKS
CYCLIZATION
ISSN:0022-3263, 1520-6904, 1520-6904
Online Access:Get more information
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Summary:Functionalized azetidines, 2,3-dihydrofurans, or the unorthodox dioxa-3-azabicyclonone-4-ene motifs are the products from transition metal-free reaction between N-oxiranylmethyl benzenesulfonamide and beta-chloro-cinnamaldehyde, depending on whether one uses either NaI/K2CO3 or LiBr/K2CO3. These ring expansion reactions involve enamide (X-ray evidence) derived from N-oxiranylmethyl benzenesulfonamide and beta-chloro-cinnamaldehyde as an intermediate. The N-oxiranylmethyl benzenesulfonamide itself upon heating gives readily separable and crystalline isomeric diazocanes that can be characterized by X-ray crystallography.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.2c00268