Vinylalumination of fluoro-carbonyl compounds

P. Veeraraghavan Ramachandran; M. Venkat Ram Reddy; Michael T. Rudd; Javier Read De Alaniz

doi:10.1016/S0040-4039(98)01974-1

Vinylalumination of fluoro-carbonyl compounds

P. Veeraraghavan Ramachandran, M. Venkat Ram Reddy, Michael T. Rudd, Javier Read De Alaniz

Chemistry & Biochemistry

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

35 Scopus citations

Abstract

Ethyl acrylate and acrylonitrile fail to undergo efficient Baylis- Hillman reaction with fluoral, but provide good yields of products with pentafluorobenzaldehyde. Alternately, unsubstituted and β-substituted [α- (ethoxycarbonyl)vinyl]aluminum react with perfluoroalkyl and -aryl aldehydes and ketones to provide the α-hydroxyalkenylated fluoro-organic compounds in good to excellent yields.

Original language	English (US)
Pages (from-to)	8791-8794
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(98)01974-1
State	Published - Nov 26 1998

Bibliographical note

Funding Information:
Acknowledgments. The financial assistance from the Purdue Borane Research Fund is gratefully acknowledged. We are thankful to Professor Herbert C. Brown for helpful discussions and encouragement.

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title = "Vinylalumination of fluoro-carbonyl compounds",

abstract = "Ethyl acrylate and acrylonitrile fail to undergo efficient Baylis- Hillman reaction with fluoral, but provide good yields of products with pentafluorobenzaldehyde. Alternately, unsubstituted and β-substituted [α- (ethoxycarbonyl)vinyl]aluminum react with perfluoroalkyl and -aryl aldehydes and ketones to provide the α-hydroxyalkenylated fluoro-organic compounds in good to excellent yields.",

author = "Ramachandran, {P. Veeraraghavan} and Reddy, {M. Venkat Ram} and Rudd, {Michael T.} and {De Alaniz}, {Javier Read}",

note = "Funding Information: Acknowledgments. The financial assistance from the Purdue Borane Research Fund is gratefully acknowledged. We are thankful to Professor Herbert C. Brown for helpful discussions and encouragement.",

year = "1998",

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doi = "10.1016/S0040-4039(98)01974-1",

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T1 - Vinylalumination of fluoro-carbonyl compounds

AU - Ramachandran, P. Veeraraghavan

AU - Reddy, M. Venkat Ram

AU - Rudd, Michael T.

AU - De Alaniz, Javier Read

N1 - Funding Information: Acknowledgments. The financial assistance from the Purdue Borane Research Fund is gratefully acknowledged. We are thankful to Professor Herbert C. Brown for helpful discussions and encouragement.

PY - 1998/11/26

Y1 - 1998/11/26

N2 - Ethyl acrylate and acrylonitrile fail to undergo efficient Baylis- Hillman reaction with fluoral, but provide good yields of products with pentafluorobenzaldehyde. Alternately, unsubstituted and β-substituted [α- (ethoxycarbonyl)vinyl]aluminum react with perfluoroalkyl and -aryl aldehydes and ketones to provide the α-hydroxyalkenylated fluoro-organic compounds in good to excellent yields.

AB - Ethyl acrylate and acrylonitrile fail to undergo efficient Baylis- Hillman reaction with fluoral, but provide good yields of products with pentafluorobenzaldehyde. Alternately, unsubstituted and β-substituted [α- (ethoxycarbonyl)vinyl]aluminum react with perfluoroalkyl and -aryl aldehydes and ketones to provide the α-hydroxyalkenylated fluoro-organic compounds in good to excellent yields.

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U2 - 10.1016/S0040-4039(98)01974-1

DO - 10.1016/S0040-4039(98)01974-1

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EP - 8794

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Vinylalumination of fluoro-carbonyl compounds

Abstract

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