Nucleophilic perfluoroalkylation of nitrones

Derek W. Nelson; Regina A. Easley; Beniamin N V Pintea

doi:10.1016/S0040-4039(98)80010-5

Nucleophilic perfluoroalkylation of nitrones

Derek W. Nelson^*, Regina A. Easley, Beniamin N V Pintea

^*Corresponding author for this work

Chemistry

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

46 Scopus citations

Abstract

New methods for perfluoroalkylation of carbon-nitrogen double bonds have been developed. Addition of (trifluoromethyl)trimethylsilane (TMSCF₃) to α,N-diarylnitrones produced α series of α-(trifluoromethyl)-N hydroxyl amines protected as their O-trimethylsilyl derivatives. An alternate procedure using pentafluoroethyllithium (F₅C₂L₁) and chlorotrimethylsilane (TMSCI) afforded O-trimethylsilyl-α-(pentafluoroethyl)-N-hydroxyl amines.

Original language	English (US)
Pages (from-to)	25-28
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	1
DOIs	https://doi.org/10.1016/S0040-4039(98)80010-5
State	Published - Jan 1 1999

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Nucleophilic perfluoroalkylation of nitrones",

abstract = "New methods for perfluoroalkylation of carbon-nitrogen double bonds have been developed. Addition of (trifluoromethyl)trimethylsilane (TMSCF3) to α,N-diarylnitrones produced α series of α-(trifluoromethyl)-N hydroxyl amines protected as their O-trimethylsilyl derivatives. An alternate procedure using pentafluoroethyllithium (F5C2L1) and chlorotrimethylsilane (TMSCI) afforded O-trimethylsilyl-α-(pentafluoroethyl)-N-hydroxyl amines.",

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T1 - Nucleophilic perfluoroalkylation of nitrones

AU - Nelson, Derek W.

AU - Easley, Regina A.

AU - Pintea, Beniamin N V

PY - 1999/1/1

Y1 - 1999/1/1

N2 - New methods for perfluoroalkylation of carbon-nitrogen double bonds have been developed. Addition of (trifluoromethyl)trimethylsilane (TMSCF3) to α,N-diarylnitrones produced α series of α-(trifluoromethyl)-N hydroxyl amines protected as their O-trimethylsilyl derivatives. An alternate procedure using pentafluoroethyllithium (F5C2L1) and chlorotrimethylsilane (TMSCI) afforded O-trimethylsilyl-α-(pentafluoroethyl)-N-hydroxyl amines.

AB - New methods for perfluoroalkylation of carbon-nitrogen double bonds have been developed. Addition of (trifluoromethyl)trimethylsilane (TMSCF3) to α,N-diarylnitrones produced α series of α-(trifluoromethyl)-N hydroxyl amines protected as their O-trimethylsilyl derivatives. An alternate procedure using pentafluoroethyllithium (F5C2L1) and chlorotrimethylsilane (TMSCI) afforded O-trimethylsilyl-α-(pentafluoroethyl)-N-hydroxyl amines.

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ER -

Nucleophilic perfluoroalkylation of nitrones

Abstract

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