Synthesis of (α,α-Difluoroalkyl)phosphonates by Displacement of Primary Triflates

David B. Berkowitz; Mari Jean Eggen; Quanrong Shen; Darby G. Sloss

doi:10.1021/jo00075a005

Synthesis of (α,α-Difluoroalkyl)phosphonates by Displacement of Primary Triflates

David B. Berkowitz, Mari Jean Eggen, Quanrong Shen, Darby G. Sloss

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

80 Scopus citations

Abstract

Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (α,α-difluoroalkyl)phosphonates in minutes at −78 °C.

Original language	English (US)
Pages (from-to)	6174-6176
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	58
Issue number	23
DOIs	https://doi.org/10.1021/jo00075a005
State	Published - 1993

ASJC Scopus subject areas

Organic Chemistry

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@article{77b9f657dfee4e6db237f6c8d81ff187,

title = "Synthesis of (α,α-Difluoroalkyl)phosphonates by Displacement of Primary Triflates",

abstract = "Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (α,α-difluoroalkyl)phosphonates in minutes at −78 °C.",

author = "Berkowitz, {David B.} and Eggen, {Mari Jean} and Quanrong Shen and Sloss, {Darby G.}",

year = "1993",

doi = "10.1021/jo00075a005",

language = "English (US)",

volume = "58",

pages = "6174--6176",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

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TY - JOUR

T1 - Synthesis of (α,α-Difluoroalkyl)phosphonates by Displacement of Primary Triflates

AU - Berkowitz, David B.

AU - Eggen, Mari Jean

AU - Shen, Quanrong

AU - Sloss, Darby G.

PY - 1993

Y1 - 1993

N2 - Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (α,α-difluoroalkyl)phosphonates in minutes at −78 °C.

AB - Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (α,α-difluoroalkyl)phosphonates in minutes at −78 °C.

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U2 - 10.1021/jo00075a005

DO - 10.1021/jo00075a005

M3 - Article

AN - SCOPUS:0001180846

SN - 0022-3263

VL - 58

SP - 6174

EP - 6176

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Synthesis of (α,α-Difluoroalkyl)phosphonates by Displacement of Primary Triflates

Abstract

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