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Exploring the reaction of iodine with α ‐diazo esters
Author(s) -
Verardo Giancarlo,
Geatti Paola,
Gambi Alberto
Publication year - 2009
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1420
Subject(s) - chemistry , diazo , alkene , carbon atom , aqueous solution , iodine , computational chemistry , quantum chemical , organic chemistry , medicinal chemistry , photochemistry , molecule , catalysis , alkyl
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 3 , afforded the Z ‐isomer of the corresponding unsaturated‐2‐iodo ester 8 . The configuration of compounds 8 was determined using the 3 J CH 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.