| Abstract
| - The addition of 2-chloroethylphosphonic acid (or ethephon), a well-known stimulating molecule forthe production of latex by Hevea brasiliensis, onto 2,3-epoxy-2-methylbutane was investigated toenhance the understandings on the addition mechanisms of reagents of alkylphosphonic acid typeonto trialkyl-substituted epoxides. It was demonstrated that the addition occurs according to athree-step mechanism including a rapid nucleophilic attack of the phosphorated anion on the mostalkyl-substituted carbon of the oxirane, followed by formation of a dioxaphospholane structure withrelease of water, and finally a hydrolytic cleavage of the dioxaphospholane cycle to generate theregioisomer 1:1 adduct where the phosphorated group is on the less alkyl-substituted carbon ofthe initial oxirane.
|
