Prev. Article Next Article Table of Contents

Article

PhCHP(MeNCH₂CH₂)₃N: A Novel Ylide for Quantitative E Selectivity in the Wittig Reaction

Supporting Info

Zhigang Wang, Guangtao Zhang, Ilia Guzei, and John G. Verkade*

Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111

J. Org. Chem., 2001, 66 (10), pp 3521–3524

DOI: 10.1021/jo0100704

Publication Date (Web): April 26, 2001

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jverkade@iastate.edu

Abstract

PhCHP(MeNCH₂CH₂)₃N (1), a semi-stabilized ylide prepared from the commercially available nonionic base P(MeNCH₂CH₂)₃N, reacts with aldehydes to give alkenes in high yield with quantitative E selectivity. In contrast with other ylides, this E selectivity is maintained despite changes in the metal ion of the ionic base used to deprotonate 1, temperature, and solvent polarity. In conjunction with structural parameters gained from the X-ray molecular structure of 1, the pathway to E selectivity in these reactions is rationalized by the Vedejs model of Wittig reaction stereochemistry.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue May 18, 2001
Received January 22, 2001

Recommend & Share

Related Content

Wittig Reactions in Water Media Employing Stabilized Ylides with Aldehydes. Synthesis of α,β-Unsaturated Esters from Mixing Aldehydes, α-Bromoesters, and Ph₃P in Aqueous NaHCO₃The Journal of Organic Chemistry
- Wittig Reactions in Water Media Employing Stabilized Ylides with Aldehydes. Synthesis of α,β-Unsaturated Esters from Mixing Aldehydes, α-Bromoesters, and Ph₃P in Aqueous NaHCO₃
  Amer El-Batta, Changchun Jiang, Wen Zhao, Robert Anness, Andrew L. Cooksy, and Mikael Bergdahl
  The Journal of Organic Chemistry 2007 72 (14), pp 5244–5259
  Abstract: Water is demonstrated to be an effective medium for the Wittig reaction over a wide range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities ...
  Abstract | Full Text HTML | Hi-Res PDF
The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsThe Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsChemical Reviews
- The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsThe Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects
  Bruce E. Maryanoff, Allen B. Reitz
  Chemical Reviews 1989 89 (4), pp 863–927
  Abstract | Hi-Res PDF

Article

PhCHP(MeNCH₂CH₂)₃N: A Novel Ylide for Quantitative E Selectivity in the Wittig Reaction