Concerted [4π + 2π] cycloaddition of (ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5) with the isomeric 2-butenedinitriles

Richard S. Glass; Wesley W. McConnell

doi:10.1021/om00089a005

Concerted [4π + 2π] cycloaddition of (ƞ⁵-C₅H₅)Fe(CO)₂(ƞ¹-C₅H₅) with the isomeric 2-butenedinitriles

Richard S. Glass, Wesley W. McConnell

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

20 Scopus citations

Abstract

Fumaronitrile and maleonitrile rapidly cycloadd to (ƞ⁵-C₅H₅)Fe(CO)₂(ƞ¹-C₅H₅) with comparable rates to afford 7-syn-[ƞ⁵-C₅H₅)Fe(CO)₂]bicyclo[2.2.1]hept-5-ene-2-exo, 3-endo-dicarbonitrile (3b) and a 1:1 mixture of 7-syn-[(ƞ⁵-C₅H₅)Fe(CO)₂]bicyclo[2.2.1]hept-5-ene-2-exo, 3-exo-dicarbonitrile (3c) and 7-syn-[ƞ⁵-C₅H₅)Fe(CO)₂]bicyclo[2.2.1]hept-5-ene-2-endo, 3-endo-dicarbonitrile (3d), respectively, in excellent yield. Mechanistic studies strongly support a concerted [4π + 2π] cycloaddition for these reactions.

Original language	English (US)
Pages (from-to)	1630-1632
Number of pages	3
Journal	Organometallics
Volume	3
Issue number	11
DOIs	https://doi.org/10.1021/om00089a005
State	Published - Jun 1984
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Concerted [4π + 2π] cycloaddition of (ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5) with the isomeric 2-butenedinitriles",

abstract = "Fumaronitrile and maleonitrile rapidly cycloadd to (ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5) with comparable rates to afford 7-syn-[ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-exo, 3-endo-dicarbonitrile (3b) and a 1:1 mixture of 7-syn-[(ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-exo, 3-exo-dicarbonitrile (3c) and 7-syn-[ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-endo, 3-endo-dicarbonitrile (3d), respectively, in excellent yield. Mechanistic studies strongly support a concerted [4π + 2π] cycloaddition for these reactions.",

author = "Glass, {Richard S.} and McConnell, {Wesley W.}",

year = "1984",

month = jun,

doi = "10.1021/om00089a005",

language = "English (US)",

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pages = "1630--1632",

journal = "Organometallics",

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T1 - Concerted [4π + 2π] cycloaddition of (ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5) with the isomeric 2-butenedinitriles

AU - Glass, Richard S.

AU - McConnell, Wesley W.

PY - 1984/6

Y1 - 1984/6

N2 - Fumaronitrile and maleonitrile rapidly cycloadd to (ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5) with comparable rates to afford 7-syn-[ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-exo, 3-endo-dicarbonitrile (3b) and a 1:1 mixture of 7-syn-[(ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-exo, 3-exo-dicarbonitrile (3c) and 7-syn-[ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-endo, 3-endo-dicarbonitrile (3d), respectively, in excellent yield. Mechanistic studies strongly support a concerted [4π + 2π] cycloaddition for these reactions.

AB - Fumaronitrile and maleonitrile rapidly cycloadd to (ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5) with comparable rates to afford 7-syn-[ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-exo, 3-endo-dicarbonitrile (3b) and a 1:1 mixture of 7-syn-[(ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-exo, 3-exo-dicarbonitrile (3c) and 7-syn-[ƞ5-C5H5)Fe(CO)2]bicyclo[2.2.1]hept-5-ene-2-endo, 3-endo-dicarbonitrile (3d), respectively, in excellent yield. Mechanistic studies strongly support a concerted [4π + 2π] cycloaddition for these reactions.

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Concerted [4π + 2π] cycloaddition of (ƞ⁵-C₅H₅)Fe(CO)₂(ƞ¹-C₅H₅) with the isomeric 2-butenedinitriles

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