Investigating the reaction of N-carbobenzoxy-O-carbobenzoxy-hydroxylamine with dimethyl sulfoxide: Formation of S,S-dimethyl-N-[(phenylmethoxy)-carbonyl] sulfoximine

Ron W. Darbeau; Noe T. Alvarez; Gregory A. Trahan; Frank R. Fronczeki

doi:10.1021/jo051158a

Investigating the reaction of N-carbobenzoxy-O-carbobenzoxy-hydroxylamine with dimethyl sulfoxide: Formation of S,S-dimethyl-N-[(phenylmethoxy)-carbonyl] sulfoximine

Ron W. Darbeau
, Noe T. Alvarez
, Gregory A. Trahan
, Frank R. Fronczeki

Penn State Altoona

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

N-Carbobenzoxy-O-carbobenzoxyhydroxylamine (1a) underwent a thermally induced reaction in DMSO in which there is net N-α-eliminative oxidation with tandem oxidative incorporation of DMSO to yield S,S-dimethyl-N-[(phenyl- methoxy)carbonyl]sulfoximine. Mechanisms for the formation of the sulfoximine are presented as well as the product characterizations, including the X-ray crystal structure.

Original language	English (US)
Pages (from-to)	9599-9602
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	23
DOIs	https://doi.org/10.1021/jo051158a
State	Published - Nov 11 2005

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo051158a

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title = "Investigating the reaction of N-carbobenzoxy-O-carbobenzoxy-hydroxylamine with dimethyl sulfoxide: Formation of S,S-dimethyl-N-[(phenylmethoxy)-carbonyl] sulfoximine",

abstract = "N-Carbobenzoxy-O-carbobenzoxyhydroxylamine (1a) underwent a thermally induced reaction in DMSO in which there is net N-α-eliminative oxidation with tandem oxidative incorporation of DMSO to yield S,S-dimethyl-N-[(phenyl- methoxy)carbonyl]sulfoximine. Mechanisms for the formation of the sulfoximine are presented as well as the product characterizations, including the X-ray crystal structure.",

author = "Darbeau, \{Ron W.\} and Alvarez, \{Noe T.\} and Trahan, \{Gregory A.\} and Fronczeki, \{Frank R.\}",

year = "2005",

month = nov,

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doi = "10.1021/jo051158a",

language = "English (US)",

volume = "70",

pages = "9599--9602",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

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Investigating the reaction of N-carbobenzoxy-O-carbobenzoxy-hydroxylamine with dimethyl sulfoxide: Formation of S,S-dimethyl-N-[(phenylmethoxy)-carbonyl] sulfoximine. / Darbeau, Ron W.; Alvarez, Noe T.; Trahan, Gregory A. et al.
In: Journal of Organic Chemistry, Vol. 70, No. 23, 11.11.2005, p. 9599-9602.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Investigating the reaction of N-carbobenzoxy-O-carbobenzoxy-hydroxylamine with dimethyl sulfoxide

T2 - Formation of S,S-dimethyl-N-[(phenylmethoxy)-carbonyl] sulfoximine

AU - Darbeau, Ron W.

AU - Alvarez, Noe T.

AU - Trahan, Gregory A.

AU - Fronczeki, Frank R.

PY - 2005/11/11

Y1 - 2005/11/11

N2 - N-Carbobenzoxy-O-carbobenzoxyhydroxylamine (1a) underwent a thermally induced reaction in DMSO in which there is net N-α-eliminative oxidation with tandem oxidative incorporation of DMSO to yield S,S-dimethyl-N-[(phenyl- methoxy)carbonyl]sulfoximine. Mechanisms for the formation of the sulfoximine are presented as well as the product characterizations, including the X-ray crystal structure.

AB - N-Carbobenzoxy-O-carbobenzoxyhydroxylamine (1a) underwent a thermally induced reaction in DMSO in which there is net N-α-eliminative oxidation with tandem oxidative incorporation of DMSO to yield S,S-dimethyl-N-[(phenyl- methoxy)carbonyl]sulfoximine. Mechanisms for the formation of the sulfoximine are presented as well as the product characterizations, including the X-ray crystal structure.

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DO - 10.1021/jo051158a

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JO - Journal of Organic Chemistry

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IS - 23

ER -

Investigating the reaction of N-carbobenzoxy-O-carbobenzoxy-hydroxylamine with dimethyl sulfoxide: Formation of S,S-dimethyl-N-[(phenylmethoxy)-carbonyl] sulfoximine

Abstract

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