Michael Addition Reactions of the Highly Functionalized Zinc-Copper Reagents RCu(CN)ZnI to (Tropone)iron Tricarbonyl Promoted by Boron Trifluoride Etherate

Ming Chang P. Yeh; Chong Chen Hwu; Chuen Her Ueng; Huei Lin Lue

doi:10.1021/om00017a041

Michael Addition Reactions of the Highly Functionalized Zinc-Copper Reagents RCu(CN)ZnI to (Tropone)iron Tricarbonyl Promoted by Boron Trifluoride Etherate

Ming Chang P. Yeh^*
, Chong Chen Hwu
, Chuen Her Ueng
, Huei Lin Lue

^*Corresponding author for this work

Department of Chemistry

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

12 Citations (Scopus)

Abstract

The zinc-copper reagents RCu(CN)ZnI, containing various functional groups such as a cyanide, ester, thio ester or benzyl, react with (tropone)iron tricarbonyl in the presence of an excess of boron trifluoride etherate to afford the Michael adducts in excellent yields. Cyano-substituted 1.4-adducts undergo an intramolecular cyclization reaction in situ, leading to highly functionalized bicyclo[5.3.0]decane and-[5.4.0]undecane derivatives, whereas treatments of an ester-substituted 1.4-adduct with lithium diisopropylamide (LDA) under an atmosphere of carbon monoxide furnishs a highly functionalized bridged bicyclo[4.2.1] nonenecarboxylic acid derivative in 88 % yield.

Original language	English
Pages (from-to)	1788-1794
Number of pages	7
Journal	Organometallics
Volume	13
Issue number	5
DOIs	https://doi.org/10.1021/om00017a041
Publication status	Published - 1994 May 1

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1021/om00017a041

Cite this

@article{0e8f1f9f52614812af86951c43e2a7a3,

title = "Michael Addition Reactions of the Highly Functionalized Zinc-Copper Reagents RCu(CN)ZnI to (Tropone)iron Tricarbonyl Promoted by Boron Trifluoride Etherate",

abstract = "The zinc-copper reagents RCu(CN)ZnI, containing various functional groups such as a cyanide, ester, thio ester or benzyl, react with (tropone)iron tricarbonyl in the presence of an excess of boron trifluoride etherate to afford the Michael adducts in excellent yields. Cyano-substituted 1.4-adducts undergo an intramolecular cyclization reaction in situ, leading to highly functionalized bicyclo[5.3.0]decane and-[5.4.0]undecane derivatives, whereas treatments of an ester-substituted 1.4-adduct with lithium diisopropylamide (LDA) under an atmosphere of carbon monoxide furnishs a highly functionalized bridged bicyclo[4.2.1] nonenecarboxylic acid derivative in 88 \% yield.",

author = "Yeh, \{Ming Chang P.\} and Hwu, \{Chong Chen\} and Ueng, \{Chuen Her\} and Lue, \{Huei Lin\}",

year = "1994",

month = may,

day = "1",

doi = "10.1021/om00017a041",

language = "English",

volume = "13",

pages = "1788--1794",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Michael Addition Reactions of the Highly Functionalized Zinc-Copper Reagents RCu(CN)ZnI to (Tropone)iron Tricarbonyl Promoted by Boron Trifluoride Etherate

AU - Yeh, Ming Chang P.

AU - Hwu, Chong Chen

AU - Ueng, Chuen Her

AU - Lue, Huei Lin

PY - 1994/5/1

Y1 - 1994/5/1

N2 - The zinc-copper reagents RCu(CN)ZnI, containing various functional groups such as a cyanide, ester, thio ester or benzyl, react with (tropone)iron tricarbonyl in the presence of an excess of boron trifluoride etherate to afford the Michael adducts in excellent yields. Cyano-substituted 1.4-adducts undergo an intramolecular cyclization reaction in situ, leading to highly functionalized bicyclo[5.3.0]decane and-[5.4.0]undecane derivatives, whereas treatments of an ester-substituted 1.4-adduct with lithium diisopropylamide (LDA) under an atmosphere of carbon monoxide furnishs a highly functionalized bridged bicyclo[4.2.1] nonenecarboxylic acid derivative in 88 % yield.

AB - The zinc-copper reagents RCu(CN)ZnI, containing various functional groups such as a cyanide, ester, thio ester or benzyl, react with (tropone)iron tricarbonyl in the presence of an excess of boron trifluoride etherate to afford the Michael adducts in excellent yields. Cyano-substituted 1.4-adducts undergo an intramolecular cyclization reaction in situ, leading to highly functionalized bicyclo[5.3.0]decane and-[5.4.0]undecane derivatives, whereas treatments of an ester-substituted 1.4-adduct with lithium diisopropylamide (LDA) under an atmosphere of carbon monoxide furnishs a highly functionalized bridged bicyclo[4.2.1] nonenecarboxylic acid derivative in 88 % yield.

UR - https://www.scopus.com/pages/publications/0000062288

UR - https://www.scopus.com/pages/publications/0000062288#tab=citedBy

U2 - 10.1021/om00017a041

DO - 10.1021/om00017a041

M3 - Article

AN - SCOPUS:0000062288

SN - 0276-7333

VL - 13

SP - 1788

EP - 1794

JO - Organometallics

JF - Organometallics

IS - 5

ER -

Michael Addition Reactions of the Highly Functionalized Zinc-Copper Reagents RCu(CN)ZnI to (Tropone)iron Tricarbonyl Promoted by Boron Trifluoride Etherate

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this