The first method for C-devinylation of aromatic systems

Sandip B. Bharate; Ramesh Mudududdla; Rohit Sharma; Ram A. Vishwakarma

doi:10.1016/j.tetlet.2013.03.064

The first method for C-devinylation of aromatic systems

Sandip B. Bharate, Ramesh Mudududdla, Rohit Sharma, Ram A. Vishwakarma

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

5 Citations (Scopus)

Abstract

This Letter describes the method for C-devinylation of aromatic systems for the first time. Vinylbenzenes on refluxing with trifluoroacetic acid produced corresponding devinylated products in excellent yields. Furthermore, 2,4,6-trimethoxy vinylbenzenes on treatment with hexamethylene tetraamine and trifluoroacetic acid exclusively produced 1,3-diformyl 2,4,6-trimethoxy benzene via tandem devinylation and diformylation reactions. A variety of aliphatic vinyl groups can be utilized but the reaction is limited to 1,3,5- trimethoxybenzene.

Original language	English
Pages (from-to)	2913-2915
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2013.03.064
Publication status	Published - 5 Jun 2013
Externally published	Yes

Keywords

Devinylation
Diformylation
Duff reaction
TFA
Vinylbenzenes

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10.1016/j.tetlet.2013.03.064

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abstract = "This Letter describes the method for C-devinylation of aromatic systems for the first time. Vinylbenzenes on refluxing with trifluoroacetic acid produced corresponding devinylated products in excellent yields. Furthermore, 2,4,6-trimethoxy vinylbenzenes on treatment with hexamethylene tetraamine and trifluoroacetic acid exclusively produced 1,3-diformyl 2,4,6-trimethoxy benzene via tandem devinylation and diformylation reactions. A variety of aliphatic vinyl groups can be utilized but the reaction is limited to 1,3,5- trimethoxybenzene.",

keywords = "Devinylation, Diformylation, Duff reaction, TFA, Vinylbenzenes",

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T1 - The first method for C-devinylation of aromatic systems

AU - Bharate, Sandip B.

AU - Mudududdla, Ramesh

AU - Sharma, Rohit

AU - Vishwakarma, Ram A.

PY - 2013/6/5

Y1 - 2013/6/5

N2 - This Letter describes the method for C-devinylation of aromatic systems for the first time. Vinylbenzenes on refluxing with trifluoroacetic acid produced corresponding devinylated products in excellent yields. Furthermore, 2,4,6-trimethoxy vinylbenzenes on treatment with hexamethylene tetraamine and trifluoroacetic acid exclusively produced 1,3-diformyl 2,4,6-trimethoxy benzene via tandem devinylation and diformylation reactions. A variety of aliphatic vinyl groups can be utilized but the reaction is limited to 1,3,5- trimethoxybenzene.

AB - This Letter describes the method for C-devinylation of aromatic systems for the first time. Vinylbenzenes on refluxing with trifluoroacetic acid produced corresponding devinylated products in excellent yields. Furthermore, 2,4,6-trimethoxy vinylbenzenes on treatment with hexamethylene tetraamine and trifluoroacetic acid exclusively produced 1,3-diformyl 2,4,6-trimethoxy benzene via tandem devinylation and diformylation reactions. A variety of aliphatic vinyl groups can be utilized but the reaction is limited to 1,3,5- trimethoxybenzene.

KW - Devinylation

KW - Diformylation

KW - Duff reaction

KW - TFA

KW - Vinylbenzenes

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DO - 10.1016/j.tetlet.2013.03.064

M3 - Article

AN - SCOPUS:84877729991

SN - 0040-4039

VL - 54

SP - 2913

EP - 2915

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

The first method for C-devinylation of aromatic systems

Abstract

Keywords

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