Exploring the reaction of iodine with  α ‐diazo esters | Zendy

Verardo Giancarlo | Zendy; Geatti Paola | Zendy; Gambi Alberto | Zendy

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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.

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