Cycloaddition of Bun3P.CS2: Direct One Pot Conversion of Strained Double Bonds to 2-Alkylidene-1,3-dithiolanes

Robert Alan Aitken; K Carcas; L Hill; Tracy Massil; SV Raut

Cycloaddition of Buⁿ₃P.CS₂: Direct One Pot Conversion of Strained Double Bonds to 2-Alkylidene-1,3-dithiolanes

Robert Alan Aitken, K Carcas, L Hill, Tracy Massil, SV Raut

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

Abstract

Reaction of the adduct between tri-n-butylphosphine and carbon disulfide 1 with norbornene gives the novel zwitterionic structure 9. In solution this dissociates to the ylide 8 which undergoes Wittig reaction with aldehydes. Using the same method, the overall conversion of the strained double bond in a variety of bicyclo[2.2.1]alkenes into 2-benzylidene-1,3-dithioles 15-24 has been achieved and the reaction is also applicable to norbornadiene, affording bisdithiolanes 29-31. (C) 1997, Elsevier Science Ltd.

Original language	English
Pages (from-to)	2261-2270
Number of pages	10
Journal	Tetrahedron
Volume	53
Issue number	6
Publication status	Published - 10 Feb 1997

Keywords

ELECTRON-DEFICIENT ALKYNES
ADDUCTS
BUN3P.CS2

Cite this

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title = "Cycloaddition of Bun3P.CS2: Direct One Pot Conversion of Strained Double Bonds to 2-Alkylidene-1,3-dithiolanes",

abstract = "Reaction of the adduct between tri-n-butylphosphine and carbon disulfide 1 with norbornene gives the novel zwitterionic structure 9. In solution this dissociates to the ylide 8 which undergoes Wittig reaction with aldehydes. Using the same method, the overall conversion of the strained double bond in a variety of bicyclo[2.2.1]alkenes into 2-benzylidene-1,3-dithioles 15-24 has been achieved and the reaction is also applicable to norbornadiene, affording bisdithiolanes 29-31. (C) 1997, Elsevier Science Ltd.",

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T1 - Cycloaddition of Bun3P.CS2: Direct One Pot Conversion of Strained Double Bonds to 2-Alkylidene-1,3-dithiolanes

AU - Aitken, Robert Alan

AU - Carcas, K

AU - Hill, L

AU - Massil, Tracy

AU - Raut, SV

PY - 1997/2/10

Y1 - 1997/2/10

N2 - Reaction of the adduct between tri-n-butylphosphine and carbon disulfide 1 with norbornene gives the novel zwitterionic structure 9. In solution this dissociates to the ylide 8 which undergoes Wittig reaction with aldehydes. Using the same method, the overall conversion of the strained double bond in a variety of bicyclo[2.2.1]alkenes into 2-benzylidene-1,3-dithioles 15-24 has been achieved and the reaction is also applicable to norbornadiene, affording bisdithiolanes 29-31. (C) 1997, Elsevier Science Ltd.

AB - Reaction of the adduct between tri-n-butylphosphine and carbon disulfide 1 with norbornene gives the novel zwitterionic structure 9. In solution this dissociates to the ylide 8 which undergoes Wittig reaction with aldehydes. Using the same method, the overall conversion of the strained double bond in a variety of bicyclo[2.2.1]alkenes into 2-benzylidene-1,3-dithioles 15-24 has been achieved and the reaction is also applicable to norbornadiene, affording bisdithiolanes 29-31. (C) 1997, Elsevier Science Ltd.

KW - ELECTRON-DEFICIENT ALKYNES

KW - ADDUCTS

KW - BUN3P.CS2

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Cycloaddition of Buⁿ₃P.CS₂: Direct One Pot Conversion of Strained Double Bonds to 2-Alkylidene-1,3-dithiolanes

Abstract

Keywords

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