Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

William B. Motherwell; Michael F. Greaney; Derek A. Tocher

doi:10.1039/b209079a

Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

William B. Motherwell, Michael F. Greaney, Derek A. Tocher

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

Abstract

Treatment of α-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the α-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced α,α-difluoro sulfides and a third led to α,α-difluoro sulfoxides. An identical pattern of reactivity was observed with the α-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from α-phenylsulfanylbutyrolactone 32.

Original language	English
Pages (from-to)	2809-2815
Number of pages	6
Journal	Journal of the Chemical Society. Perkin Transactions 1
Issue number	24
DOIs	https://doi.org/10.1039/b209079a
Publication status	Published - 21 Dec 2002

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title = "Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene",

abstract = "Treatment of α-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the α-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced α,α-difluoro sulfides and a third led to α,α-difluoro sulfoxides. An identical pattern of reactivity was observed with the α-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from α-phenylsulfanylbutyrolactone 32.",

author = "Motherwell, {William B.} and Greaney, {Michael F.} and Tocher, {Derek A.}",

note = "CAPLUS AN 2002:963598(Journal)",

year = "2002",

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doi = "10.1039/b209079a",

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publisher = "Chemical Society",

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T1 - Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

AU - Motherwell, William B.

AU - Greaney, Michael F.

AU - Tocher, Derek A.

N1 - CAPLUS AN 2002:963598(Journal)

PY - 2002/12/21

Y1 - 2002/12/21

N2 - Treatment of α-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the α-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced α,α-difluoro sulfides and a third led to α,α-difluoro sulfoxides. An identical pattern of reactivity was observed with the α-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from α-phenylsulfanylbutyrolactone 32.

AB - Treatment of α-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the α-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced α,α-difluoro sulfides and a third led to α,α-difluoro sulfoxides. An identical pattern of reactivity was observed with the α-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from α-phenylsulfanylbutyrolactone 32.

U2 - 10.1039/b209079a

DO - 10.1039/b209079a

M3 - Article

SN - 1472-7781

SP - 2809

EP - 2815

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 24

ER -

Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

Abstract

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