Journal of organometallic chemistry

An organometallic route to (±) 3-p-toluenesulfinyl-2-pyrone

GH Posner, W Harrison

Index: Posner, Gary H.; Harrison, Wayne Journal of Organometallic Chemistry, 1985 , vol. 285, p. C27 - C30

Full Text: HTML

Citation Number: 0

Abstract

Abstract 3-Bromo-2-pyrone reacts with dimethylcopperlithium and then with p-tolyl p- toluenethiosulfonate to form 3-p-toluenethio-2-pyrone. Organocopper species are likely intermediates in this reaction. Oxidation of the sulfide produces (±)-3-p-toluenesulfinyl-2- pyrone. The overall process involves an important and useful umpolung, a reversal of reactivity at C (3) of the pyrone ring from an electrophilic center to a nucleophilic center.

Related Articles:

Synthesis and conformational analysis of a ribo-type cyclohexenyl nucleoside

[Journal of Organic Chemistry, , vol. 70, # 12 p. 4591 - 4597]

One step preparation of bromo-2-pyrones via bromo-decarboxylation of 2-pyrone-carboxylic acids

[Cho, Cheon-Gyu; Park, Jung-Sang; Jung, In-Hak; Lee, Haiwon Tetrahedron Letters, 2001 , vol. 42, # 6 p. 1065 - 1067]

3-bromo-2-pyrone: an easily prepared chameleon diene and a synthetic equivalent of 2-pyrone in thermal diels-alder cycloadditions

[Posner, Gary H.; Nelson, Todd D.; Kinter, Chris M.; Afarinkia, Kamyar Tetrahedron Letters, 1991 , vol. 32, # 39 p. 5295 - 5298]

3-bromo-2-pyrone: an easily prepared chameleon diene and a synthetic equivalent of 2-pyrone in thermal diels-alder cycloadditions

[Posner, Gary H.; Nelson, Todd D.; Kinter, Chris M.; Afarinkia, Kamyar Tetrahedron Letters, 1991 , vol. 32, # 39 p. 5295 - 5298]

More Articles...