Document Type
Article
Publication Date
2004
Publication Title
Canadian Journal of Chemistry-Revue Canadienne De Chimie
Volume
82
Issue
2
First Page
366
Last Page
374
Abstract
Bis(hexacarbonyldicobalt) complexes of benzyl ether - methyl ether or benzyl ether - acetate derivatives of hepta-2,5-diyne-1,7-diols undergo selective Lewis-acid-mediated Nicholas reactions with enol silanes, silyl ketene acetals, and allylstannanes, preferentially replacing the methyl ether or acetate function. Hydride nucleophiles are similarly incorporated selectively using a benzyl ether - alcohol derivative. Subsequent Nicholas reaction at the benzyloxy-bearing site may be accomplished with an identical or a different nucleophile, affording skipped 1,4-diyne-Co-4(CO)(12) complexes. In instances of lower selectivity for monosubstitution reactions with benzyl ethers, reverting to the use of a menthyl ether - methyl ether complex gives much improved selectivity for methyl ether substitution.
DOI
10.1139/v03-209
Recommended Citation
Guo, Richard; Gibe, Romelo; and Green, James R.. (2004). Mono- and disubstitutions of (hepta-2,5-diyne-1,7-diol) bis(dicobalt) derivatives - Selectivity in Nicholas reactions. Canadian Journal of Chemistry-Revue Canadienne De Chimie, 82 (2), 366-374.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/14
Comments
The article available for download is the authors accepted manuscript. The definitive version is published in the Canadian Journal of Chemistry - Revue Canadienne De Chimie and is available here. Copyright (2012) Canadian Science Publishing.