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Exploring the reaction of iodine with α-diazo esters.

Authors :
Verardo, Giancarlo
Geatti, Paola
Gambi, Alberto
Source :
Journal of Physical Organic Chemistry; Jan2009, Vol. 22 Issue 1, p24-30, 7p, 6 Diagrams, 1 Chart
Publication Year :
2009

Abstract

In this paper we describe the unprecedented reaction between α-diazo esters 1 and iodine. The reaction, carried out in the presence of aqueous NaHCO<subscript>3</subscript>, afforded the Z-isomer of the corresponding unsaturated-2-iodo ester 8. The configuration of compounds 8 was determined using the <superscript>3</superscript>J<subscript>C&bond;H</subscript> coupling between carbonyl carbon atom and alkene proton. Mechanistic considerations accounting for the observed phenomena and including quantum chemical calculations are proposed. Copyright © 2008 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
08943230
Volume :
22
Issue :
1
Database :
Complementary Index
Journal :
Journal of Physical Organic Chemistry
Publication Type :
Academic Journal
Accession number :
35678222
Full Text :
https://doi.org/10.1002/poc.1420