Oxidative cleavage of conformationally rigid vinyl orthoesters. Evidence for primary and secondary stereoelectronic control in the cleavage of tetrahedral intermediates-Reference-Cited by-同舟云学术

Oxidative cleavage of conformationally rigid vinyl orthoesters. Evidence for primary and secondary stereoelectronic control in the cleavage of tetrahedral intermediates

Published:1980-05-15 Issue:10 Volume:58 Page:1051-1058
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Deslongchamps Pierre,Beaulieu Normand,Chênevert Robert,Dickinson Robert A.

Abstract

Permanganate oxidation of either axial vinyl orthoester 1 or equatorial vinyl orthoester 7 yields essentially hydroxy ester 5 only. These results can be interpreted on the basis of stereoelectronic effects which control the cleavage of tetrahedral intermediates 2 and 8.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v80-164

Cited by 21 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis and mesomorphic investigation of calamitic liquid crystalline system ethyl-[4-(4′-decyloxy)benzoyloxy]-benzoate (4-EDBB): A temperature dependent micro-Raman study and DFT calculations;Vibrational Spectroscopy;2013-11

2. An Evaluation of Peptide-Bond Isosteres;ChemBioChem;2011-07-12

3. Oxazoles XXI. Three Ester Ammonium Salts Resulting from the Rupture of an Oxazoline Ring;Journal of Chemical Crystallography;2009-10-21

4. Structure and phase transition in self-assembled films of an anti-ferroelectric liquid crystal studied by two-dimensional correlation FTIR spectroscopy;Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy;2005-03

5. Is There Stereoelectronic Control in Formation and Cleavage of Tetrahedral Intermediates?;Accounts of Chemical Research;2001-11-30