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Frank Jensen

Chemistry of singlet oxygen. 49. Photooxidation of thiiranes

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Chemistry of singlet oxygen. 49. Photooxidation of thiiranes. / Jensen, F.; Foote, Christopher S.

In: Journal of the American Chemical Society, Vol. 109, No. 5, 1987, p. 1478-1485.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

Harvard

Jensen, F & Foote, CS 1987, 'Chemistry of singlet oxygen. 49. Photooxidation of thiiranes', Journal of the American Chemical Society, vol. 109, no. 5, pp. 1478-1485. https://doi.org/10.1021/ja00239a030

APA

Jensen, F., & Foote, C. S. (1987). Chemistry of singlet oxygen. 49. Photooxidation of thiiranes. Journal of the American Chemical Society, 109(5), 1478-1485. https://doi.org/10.1021/ja00239a030

CBE

Jensen F, Foote CS. 1987. Chemistry of singlet oxygen. 49. Photooxidation of thiiranes. Journal of the American Chemical Society. 109(5):1478-1485. https://doi.org/10.1021/ja00239a030

MLA

Jensen, F. and Christopher S. Foote. "Chemistry of singlet oxygen. 49. Photooxidation of thiiranes". Journal of the American Chemical Society. 1987, 109(5). 1478-1485. https://doi.org/10.1021/ja00239a030

Vancouver

Jensen F, Foote CS. Chemistry of singlet oxygen. 49. Photooxidation of thiiranes. Journal of the American Chemical Society. 1987;109(5):1478-1485. https://doi.org/10.1021/ja00239a030

Author

Jensen, F. ; Foote, Christopher S. / Chemistry of singlet oxygen. 49. Photooxidation of thiiranes. In: Journal of the American Chemical Society. 1987 ; Vol. 109, No. 5. pp. 1478-1485.

Bibtex

@article{576e3ea186f9409caca802e47145b6ae,
title = "Chemistry of singlet oxygen. 49. Photooxidation of thiiranes",
abstract = "The reaction between thiiranes and singlet oxygen has been investigated. Diphenylthiirane is unreactive, but simple alkyl thiiranes react readily, even at low temperature. The products depend on solvent and substrate concentration. In nonnucleophilic solvents, the primary product is the thiirane oxide. In methanol, the primary products are sulfinic esters at low substrate concentration and thiirane oxide at high concentration. It is suggested that the reaction proceeds via an intermediate, for which we assign a peroxythiirane oxide structure. The structures of potential intermediates have been calculated at the ab initio level using a 3-21 G basis set. The reaction mechanism is discussed on the basis of Frontier Molecular Orbital theory and ab initio calculations.",
author = "F. Jensen and Foote, {Christopher S.}",
year = "1987",
doi = "10.1021/ja00239a030",
language = "English",
volume = "109",
pages = "1478--1485",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "ACS Publications",
number = "5",

}

RIS

TY - JOUR

T1 - Chemistry of singlet oxygen. 49. Photooxidation of thiiranes

AU - Jensen, F.

AU - Foote, Christopher S.

PY - 1987

Y1 - 1987

N2 - The reaction between thiiranes and singlet oxygen has been investigated. Diphenylthiirane is unreactive, but simple alkyl thiiranes react readily, even at low temperature. The products depend on solvent and substrate concentration. In nonnucleophilic solvents, the primary product is the thiirane oxide. In methanol, the primary products are sulfinic esters at low substrate concentration and thiirane oxide at high concentration. It is suggested that the reaction proceeds via an intermediate, for which we assign a peroxythiirane oxide structure. The structures of potential intermediates have been calculated at the ab initio level using a 3-21 G basis set. The reaction mechanism is discussed on the basis of Frontier Molecular Orbital theory and ab initio calculations.

AB - The reaction between thiiranes and singlet oxygen has been investigated. Diphenylthiirane is unreactive, but simple alkyl thiiranes react readily, even at low temperature. The products depend on solvent and substrate concentration. In nonnucleophilic solvents, the primary product is the thiirane oxide. In methanol, the primary products are sulfinic esters at low substrate concentration and thiirane oxide at high concentration. It is suggested that the reaction proceeds via an intermediate, for which we assign a peroxythiirane oxide structure. The structures of potential intermediates have been calculated at the ab initio level using a 3-21 G basis set. The reaction mechanism is discussed on the basis of Frontier Molecular Orbital theory and ab initio calculations.

UR - http://www.scopus.com/inward/record.url?scp=0000340836&partnerID=8YFLogxK

U2 - 10.1021/ja00239a030

DO - 10.1021/ja00239a030

M3 - Journal article

VL - 109

SP - 1478

EP - 1485

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 5

ER -