2-Acetoxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline and acetoxy(methoxy)carbene-Reference-Cited by-同舟云学术

2-Acetoxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline and acetoxy(methoxy)carbene

Published:2003-12-01 Issue:12 Volume:81 Page:1438-1442
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Czardybon Wojciech,Klys Arkadiusz,Warkentin John,Werstiuk Nick Henry

Abstract

2-Acetoxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline undergoes two competitive 1,3-dipolar cycloreversions at 110 °C. It loses N2, presumably to afford a short-lived carbonyl ylide that fragments to acetone and acetoxy(methoxy)carbene. It also forms 2-diazopropane and the appropriate mixed anhydride. It is the only currently known source of acetoxy(methoxy)carbene. Key words: acetoxy(methoxy)carbene, 2-diazopropane, 1,3-dipolar cycloreversion.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v03-126

Reference15 articles.

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2. Acetoxycarbenes: Modified Oxacarbenes with Enhanced Reactivity

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4. Structure-reactivity dependence in the rearrangements of a family of alkylacetoxycarbenes

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