Metal hydride reduction of some σ- and π-allyl and benzyl derivatives of mercury and palladium

L. Bullpitt M. and Kitching W. (1972) Metal hydride reduction of some σ- and π-allyl and benzyl derivatives of mercury and palladium. Journal of Organometallic Chemistry, 46 1: 21-29. doi:10.1016/S0022-328X(00)90472-8


Author L. Bullpitt M.
Kitching W.
Title Metal hydride reduction of some σ- and π-allyl and benzyl derivatives of mercury and palladium
Journal name Journal of Organometallic Chemistry   Check publisher's open access policy
ISSN 0022-328X
Publication date 1972-12-01
Sub-type Article (original research)
DOI 10.1016/S0022-328X(00)90472-8
Volume 46
Issue 1
Start page 21
End page 29
Total pages 9
Subject 1303 Specialist Studies in Education
1501 Accounting, Auditing and Accountability
1604 Human Geography
1605 Policy and Administration
1606 Political Science
2501 Materials Science (miscellaneous)
2505 Materials Chemistry
Abstract The reductionof 2-butenyl-mercuric (crotyl-mercuric) systems, RHgX where X = Cl, Br, OCOCH3, by sodium borohydride and trimethyltin hydride has been investigated and under all conditions examined, 1-butene is the sole organic product. Crotylmercuric hydride seems likely to form and then to undergo either intramolecular transfer of hydrogen from mercury to carbon in an SNi′ manner, or SN2′ displacement of mercury by some hydride species leading to 1-butene, or reactions producing crotyl-Hg1 or crotyl-Hg- which are cleaved by water or methanol to again yield 1-butene. π-Crotylpalladium chloride on reduction yields only trans-2-butene, but in the presence of increasing concentratins of triphenylphosphine, which promotes the π ⇄ σ equilibrium of allylpalladium chloride systems, substantial amounts of 1-butene are formed. In aqueous tetrahydrofuran, sodium borohydride converts venzylmercuric chloride cleanly to divenzylmercury. Reduction by tetramethylammonium borohydride in benzene, yields toluene (70%) and dibenzylmercury(30%) whereas toluene was the only product from trimethyltin hydride reduction.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
Versions
Version Filter Type
Citation counts: Scopus Citation Count Cited 17 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Created: Tue, 05 Jul 2016, 11:03:25 EST by System User