Affordable Access

Publisher Website

A novel ambident reactivity of azolylacroleins

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
63
Issue
22
Identifiers
DOI: 10.1016/j.tet.2007.03.098
Keywords
  • Azolyltriene
  • Wittig Reaction
  • Phosphorane
  • Ab Initio Calculation

Abstract

Abstract Reaction of azolylacroleins with phosphoranes bearing a conjugated double bond was found to yield either azolyltrienes in a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambident reactivity was found to be dependent on the substituent of the phosphorane, which was rationalized by ab initio (DFT) calculation of the atomic charges of the reaction centres.

There are no comments yet on this publication. Be the first to share your thoughts.

Statistics

Seen <100 times
0 Comments

More articles like this

Ambident reactivity of the nitrite ion revisited.

on Angewandte Chemie Internationa... Jul 18, 2005

Farewell to the HSAB treatment of ambident reactiv...

on Angewandte Chemie Internationa... Jul 11, 2011

Marcus analysis of ambident reactivity.

on Angewandte Chemie Internationa... Jul 12, 2010
More articles like this..