Reactions of cyclopropenone derivatives with a cyclopentadienylcobalt(I) chelate: Formation of a cobaltacyclobutenone and a transformation of 2,2-dimethoxycyclopropenone to methyl acrylate at cobalt

Research output: Contribution to journalArticleResearchpeer review

Authors

Research Organisations

View graph of relations

Details

Original languageEnglish
Pages (from-to)2108-2113
Number of pages6
JournalOrganometallics
Volume19
Issue number11
Publication statusPublished - 28 Apr 2000

Abstract

Reactions of cyclopropenone derivatives with the [2-(di-tert-butylphosphanyl)ethyl]cyclopentadienylcobalt(I) chelate system were investigated. Ethene complex 2 reacts with diphenylcyclopropenone under cobalt insertion to give cobaltacyclobutenone chelate complex 6 in 91% yield. 6 was characterized crystallographically and shows a structure similar to that of a known platinacyclobutenone. Thermoanalysis of 6 indicated a reaction at elevated temperature, which was shown to be a cycloreversion at 60°C leading to known diphenylethyne and carbonyl complexes 7 and 9. Attempts to reduce the metallacyclobutenone with lithium tetrahydridoaluminate resulted in the cycloreversion reaction at a temperature as low as -100 to -90°C, the lithium cation acting as a Lewis acid. The reaction of dimethoxycyclopropene complex 4 with zinc triflate unexpectedly resulted in the formation of methyl acrylate complex 13, which was characterized crystallographically.

ASJC Scopus subject areas

Cite this

Reactions of cyclopropenone derivatives with a cyclopentadienylcobalt(I) chelate: Formation of a cobaltacyclobutenone and a transformation of 2,2-dimethoxycyclopropenone to methyl acrylate at cobalt. / Foerstner, Jan; Kakoschke, Alf; Wartchow, Rudolf et al.
In: Organometallics, Vol. 19, No. 11, 28.04.2000, p. 2108-2113.

Research output: Contribution to journalArticleResearchpeer review

Download
@article{b3d83e1ebbee45b9af0a386a7fbbd227,
title = "Reactions of cyclopropenone derivatives with a cyclopentadienylcobalt(I) chelate: Formation of a cobaltacyclobutenone and a transformation of 2,2-dimethoxycyclopropenone to methyl acrylate at cobalt",
abstract = "Reactions of cyclopropenone derivatives with the [2-(di-tert-butylphosphanyl)ethyl]cyclopentadienylcobalt(I) chelate system were investigated. Ethene complex 2 reacts with diphenylcyclopropenone under cobalt insertion to give cobaltacyclobutenone chelate complex 6 in 91% yield. 6 was characterized crystallographically and shows a structure similar to that of a known platinacyclobutenone. Thermoanalysis of 6 indicated a reaction at elevated temperature, which was shown to be a cycloreversion at 60°C leading to known diphenylethyne and carbonyl complexes 7 and 9. Attempts to reduce the metallacyclobutenone with lithium tetrahydridoaluminate resulted in the cycloreversion reaction at a temperature as low as -100 to -90°C, the lithium cation acting as a Lewis acid. The reaction of dimethoxycyclopropene complex 4 with zinc triflate unexpectedly resulted in the formation of methyl acrylate complex 13, which was characterized crystallographically.",
author = "Jan Foerstner and Alf Kakoschke and Rudolf Wartchow and Holger Butensch{\"o}n",
year = "2000",
month = apr,
day = "28",
doi = "10.1021/om0000818",
language = "English",
volume = "19",
pages = "2108--2113",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "11",

}

Download

TY - JOUR

T1 - Reactions of cyclopropenone derivatives with a cyclopentadienylcobalt(I) chelate

T2 - Formation of a cobaltacyclobutenone and a transformation of 2,2-dimethoxycyclopropenone to methyl acrylate at cobalt

AU - Foerstner, Jan

AU - Kakoschke, Alf

AU - Wartchow, Rudolf

AU - Butenschön, Holger

PY - 2000/4/28

Y1 - 2000/4/28

N2 - Reactions of cyclopropenone derivatives with the [2-(di-tert-butylphosphanyl)ethyl]cyclopentadienylcobalt(I) chelate system were investigated. Ethene complex 2 reacts with diphenylcyclopropenone under cobalt insertion to give cobaltacyclobutenone chelate complex 6 in 91% yield. 6 was characterized crystallographically and shows a structure similar to that of a known platinacyclobutenone. Thermoanalysis of 6 indicated a reaction at elevated temperature, which was shown to be a cycloreversion at 60°C leading to known diphenylethyne and carbonyl complexes 7 and 9. Attempts to reduce the metallacyclobutenone with lithium tetrahydridoaluminate resulted in the cycloreversion reaction at a temperature as low as -100 to -90°C, the lithium cation acting as a Lewis acid. The reaction of dimethoxycyclopropene complex 4 with zinc triflate unexpectedly resulted in the formation of methyl acrylate complex 13, which was characterized crystallographically.

AB - Reactions of cyclopropenone derivatives with the [2-(di-tert-butylphosphanyl)ethyl]cyclopentadienylcobalt(I) chelate system were investigated. Ethene complex 2 reacts with diphenylcyclopropenone under cobalt insertion to give cobaltacyclobutenone chelate complex 6 in 91% yield. 6 was characterized crystallographically and shows a structure similar to that of a known platinacyclobutenone. Thermoanalysis of 6 indicated a reaction at elevated temperature, which was shown to be a cycloreversion at 60°C leading to known diphenylethyne and carbonyl complexes 7 and 9. Attempts to reduce the metallacyclobutenone with lithium tetrahydridoaluminate resulted in the cycloreversion reaction at a temperature as low as -100 to -90°C, the lithium cation acting as a Lewis acid. The reaction of dimethoxycyclopropene complex 4 with zinc triflate unexpectedly resulted in the formation of methyl acrylate complex 13, which was characterized crystallographically.

UR - http://www.scopus.com/inward/record.url?scp=0001281596&partnerID=8YFLogxK

U2 - 10.1021/om0000818

DO - 10.1021/om0000818

M3 - Article

AN - SCOPUS:0001281596

VL - 19

SP - 2108

EP - 2113

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 11

ER -

By the same author(s)