Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes

Samantha J Brown; Stuart Corr; Jonathan Percy

doi:10.1016/S0040-4039(00)00804-2

Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes

Samantha J Brown, Stuart Corr, Jonathan Percy

Pure And Applied Chemistry

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

21 Citations (Scopus)

Abstract

Fluoro- and di-fluoro allylic alcohols obtained from HFC-134a and HCFC-133a were transformed through [3,3]-sigmatropic rearrangements into 3-fluoro-4-halo-4-alkenoates with variable substitution at the 2- and 3-positions. Ozonolysis of the haloalkenes afforded the corresponding acyl halides which could be trapped with nucleophiles to afford fluorinated succinic acid derivatives in which the two carboxylic acid groups were differentiated.

Original language	English
Pages (from-to)	5269-5273
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4039(00)00804-2
Publication status	Published - 1 Jul 2000

Keywords

allylic alcohols
ozonolysis
haloalkenes

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10.1016/S0040-4039(00)00804-2

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title = "Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes",

abstract = "Fluoro- and di-fluoro allylic alcohols obtained from HFC-134a and HCFC-133a were transformed through [3,3]-sigmatropic rearrangements into 3-fluoro-4-halo-4-alkenoates with variable substitution at the 2- and 3-positions. Ozonolysis of the haloalkenes afforded the corresponding acyl halides which could be trapped with nucleophiles to afford fluorinated succinic acid derivatives in which the two carboxylic acid groups were differentiated.",

keywords = "allylic alcohols, ozonolysis, haloalkenes",

author = "Brown, {Samantha J} and Stuart Corr and Jonathan Percy",

year = "2000",

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doi = "10.1016/S0040-4039(00)00804-2",

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T1 - Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes

AU - Brown, Samantha J

AU - Corr, Stuart

AU - Percy, Jonathan

PY - 2000/7/1

Y1 - 2000/7/1

N2 - Fluoro- and di-fluoro allylic alcohols obtained from HFC-134a and HCFC-133a were transformed through [3,3]-sigmatropic rearrangements into 3-fluoro-4-halo-4-alkenoates with variable substitution at the 2- and 3-positions. Ozonolysis of the haloalkenes afforded the corresponding acyl halides which could be trapped with nucleophiles to afford fluorinated succinic acid derivatives in which the two carboxylic acid groups were differentiated.

AB - Fluoro- and di-fluoro allylic alcohols obtained from HFC-134a and HCFC-133a were transformed through [3,3]-sigmatropic rearrangements into 3-fluoro-4-halo-4-alkenoates with variable substitution at the 2- and 3-positions. Ozonolysis of the haloalkenes afforded the corresponding acyl halides which could be trapped with nucleophiles to afford fluorinated succinic acid derivatives in which the two carboxylic acid groups were differentiated.

KW - allylic alcohols

KW - ozonolysis

KW - haloalkenes

U2 - 10.1016/S0040-4039(00)00804-2

DO - 10.1016/S0040-4039(00)00804-2

M3 - Article

VL - 41

SP - 5269

EP - 5273

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 27

ER -

Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes

Abstract

Keywords

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