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

Citation
J. Foerstner et al., 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, ORGANOMETAL, 19(11), 2000, pp. 2108-2113
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
02767333 → ACNP
Volume
19
Issue
11
Year of publication
2000
Pages
2108 - 2113
Database
ISI
SICI code
0276-7333(20000529)19:11<2108:ROCDWA>2.0.ZU;2-3
Abstract
Reactions of cyclopropenone derivatives with the [2-(di-tert-butylphosphany l)ethyl] cyclopentadienylcobalt(I) chelate system were investigated. Ethene complex 2 reacts with diphenylcyclopropenone under cobalt insertion to giv e cobaltacyclobutenone chelate complex 6 in 91% yield. 6 was characterized crystallographically and shows a structure similar to that of a known plati nacyclobutenone. Thermoanalysis of 6 indicated a reaction at elevated tempe rature, which was shown to be a cycloreversion at 60 degrees C leading to k nown diphenylethyne and carbonyl complexes 7 and 9. Attempts to reduce the metallacyclobutenone with lithium tetrahydridoaluminate resulted in the cyc loreversion reaction at a temperature as low as -100 to -90 degrees C, the lithium cation acting as a Lewis acid. The reaction of dimethoxycyclopropen e complex 4 with zinc triflate unexpectedly resulted in the formation of me thyl acrylate complex 13, which was characterized crystallographically.