New path for the decomposition of bipolar adducts formed by the reaction of olefin oxides with diphenyl-?-hydroxyalkylphosphines

Exchange reaction of oxiranes with β-hydroxyalkyl sulfides, selenides,-amines, and-phosphines

“…Adducts of the R3P+CCO -type are known to arise when phosphonium ylides react with carbonyl compounds zz or oxiranes react with tertiary phosphines. 46 They decompose according to four pathways to give the following products: alkenes and phosphine oxides, 46 ketones and phosphines, 47 ylides and carbonyl compounds, 46 or oxiranes and phosphines 45,45 (Scheme 21). This type of decomposition is also known for analogous compounds of nitrogen 38 and arsenic.…”

“…The degree of conversion of the starting phosphine was -83%; ethylene oxide accounts for 5%. 45 The formation of ethytene oxide is presented in Scheme 20.…”