3,4-Didehydropyridine plus cyclopentadiene: [2+2] or [4+2]-cycloaddition ?

Manfred G. Reinecke; E. Sherwood Brown; Bruce P. Capehart; David E. Minter; Richard K. Freeman

doi:10.1016/S0040-4020(01)81429-0

3,4-Didehydropyridine plus cyclopentadiene: [2+2] or [4+2]-cycloaddition ?

Manfred G. Reinecke, E. Sherwood Brown, Bruce P. Capehart, David E. Minter, Richard K. Freeman

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

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Abstract

3, 4-Didehydropyridine (2) generated from two precursors (6 and 7) of the diazonium carboxylate 5 reacts with cyclopentadiene to give the [ 4+2 ] -cyclo-addition product 3 rather than the [2+2]-adduct 4 proposed in the literature. The structure of 3 was supported by complete proton and carbon NMR assignments made with the aid of decoupling and 2D experiments.

Original language	English (US)
Pages (from-to)	5675-5680
Number of pages	6
Journal	Tetrahedron
Volume	44
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4020(01)81429-0
State	Published - 1988

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "3,4-Didehydropyridine plus cyclopentadiene: [2+2] or [4+2]-cycloaddition ?",

abstract = "3, 4-Didehydropyridine (2) generated from two precursors (6 and 7) of the diazonium carboxylate 5 reacts with cyclopentadiene to give the [ 4+2 ] -cyclo-addition product 3 rather than the [2+2]-adduct 4 proposed in the literature. The structure of 3 was supported by complete proton and carbon NMR assignments made with the aid of decoupling and 2D experiments.",

author = "Reinecke, {Manfred G.} and {Sherwood Brown}, E. and Capehart, {Bruce P.} and Minter, {David E.} and Freeman, {Richard K.}",

year = "1988",

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volume = "44",

pages = "5675--5680",

journal = "Tetrahedron",

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TY - JOUR

T1 - 3,4-Didehydropyridine plus cyclopentadiene

T2 - [2+2] or [4+2]-cycloaddition ?

AU - Reinecke, Manfred G.

AU - Sherwood Brown, E.

AU - Capehart, Bruce P.

AU - Minter, David E.

AU - Freeman, Richard K.

PY - 1988

Y1 - 1988

N2 - 3, 4-Didehydropyridine (2) generated from two precursors (6 and 7) of the diazonium carboxylate 5 reacts with cyclopentadiene to give the [ 4+2 ] -cyclo-addition product 3 rather than the [2+2]-adduct 4 proposed in the literature. The structure of 3 was supported by complete proton and carbon NMR assignments made with the aid of decoupling and 2D experiments.

AB - 3, 4-Didehydropyridine (2) generated from two precursors (6 and 7) of the diazonium carboxylate 5 reacts with cyclopentadiene to give the [ 4+2 ] -cyclo-addition product 3 rather than the [2+2]-adduct 4 proposed in the literature. The structure of 3 was supported by complete proton and carbon NMR assignments made with the aid of decoupling and 2D experiments.

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U2 - 10.1016/S0040-4020(01)81429-0

DO - 10.1016/S0040-4020(01)81429-0

M3 - Article

AN - SCOPUS:0009970320

SN - 0040-4020

VL - 44

SP - 5675

EP - 5680

JO - Tetrahedron

JF - Tetrahedron

IS - 18

ER -

3,4-Didehydropyridine plus cyclopentadiene: [2+2] or [4+2]-cycloaddition ?

Abstract

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