Deoxygenation and desulfurization of organic compounds via transition metal atom cocondensation

Shigeo Togashi, John G. Fulcher, Bong-Rae Cho, Minoru Hasegawa, J. A. Gladysz

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Reactions resulting from the cocondensation of transition metal atoms with a variety of oxygen- and sulfur-containing organic compounds are surveyed. Alkenes are the major or exclusive volatile products when epoxides are reacted with Ti, V, Cr, Co, and Ni atoms. 2,6-Dimethylpyridine N-oxide and dimethyl sulfoxide undergo deoxygenation upon cocondensation with chromium, but diisopropyl ether and decyl methyl ether do not. Dibenzyl ether yields bis(η 6-dibenzyl ether)chromium(0) with Cr atoms, but dibenzyl sulfide undergoes desulfurization. Cyclohexanone and cycloheptanone afford low yields of reductive coupling and aldol products when cocondensed with Cr, Co, and Ni atoms. Nitro- and nitrosoarenes are deoxygenated to coupled azo and azoxy products with Cr atoms. Carbazole (3) is obtained from 2-nitrosobiphenyl, implicating nitrene or nitrenoid intermediates. Whereas isocyanides are not formed from isocyanates and metal atoms, they are produced when isothiocyanates are cocondensed with Cr and V atoms.

Original languageEnglish
Pages (from-to)3044-3053
Number of pages10
JournalJournal of Organic Chemistry
Volume45
Issue number15
Publication statusPublished - 1980 Dec 1
Externally publishedYes

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Chromium
Desulfurization
Organic compounds
Transition metals
Metals
Isothiocyanates
Isocyanates
Methyl Ethers
Atoms
Epoxy Compounds
Cyanides
Alkenes
Dimethyl Sulfoxide
Sulfur
Oxides
Oxygen
dibenzyl ether
cycloheptanone
diisopropyl ether
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Togashi, S., Fulcher, J. G., Cho, B-R., Hasegawa, M., & Gladysz, J. A. (1980). Deoxygenation and desulfurization of organic compounds via transition metal atom cocondensation. Journal of Organic Chemistry, 45(15), 3044-3053.

Deoxygenation and desulfurization of organic compounds via transition metal atom cocondensation. / Togashi, Shigeo; Fulcher, John G.; Cho, Bong-Rae; Hasegawa, Minoru; Gladysz, J. A.

In: Journal of Organic Chemistry, Vol. 45, No. 15, 01.12.1980, p. 3044-3053.

Research output: Contribution to journalArticle

Togashi, S, Fulcher, JG, Cho, B-R, Hasegawa, M & Gladysz, JA 1980, 'Deoxygenation and desulfurization of organic compounds via transition metal atom cocondensation', Journal of Organic Chemistry, vol. 45, no. 15, pp. 3044-3053.
Togashi, Shigeo ; Fulcher, John G. ; Cho, Bong-Rae ; Hasegawa, Minoru ; Gladysz, J. A. / Deoxygenation and desulfurization of organic compounds via transition metal atom cocondensation. In: Journal of Organic Chemistry. 1980 ; Vol. 45, No. 15. pp. 3044-3053.
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