OXYMERCURATION OF CIS AND TRANS-2-BUTENE,
Abstract
Equilibrium constants were measured for the reaction of cis and trans-2-butene with aqueous mercurie chloride to give three and erythro-3-chloromercuri-2-butanol. The three compound is thermodynamically more stable by 0.4 kcal./mole in aqueous solution. This was construed to require that the chloromercuri group and the hydroxyl group prefer a gauche orientation in solution. The deoxymercuration of three and erythro-3-iodomercuri-2butanols by non-halogen acids proceed at nearly identical rates. They give the starting olefins without crosscontamination. This is interpreted in terms polarization of the terminal methyl groups. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 01, 1960
- Accession Number
- AD0613312
Entities
People
- Larry L. Schaleger
- Maurice M. Kreevoy
Organizations
- University of Minnesota