Wojciech Dmowski
1982
Citations
0
Influential Citations
11
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract 1-Phenylpentafluoropropene and its para-substituted analogs 1 are susceptible to nucleophilic attack at both vinylic carbon atoms C-1 and C-2. They react with ethanolio sodium ethoxide to give predominantly substitution products, 1-ethoxy-1-phenyltetrafluoropropenes 2 and 2-ethoxy-1-phenyltetrafluoropropenes 3 , with only little formation of adducts, viz . 2-ethoxy-1H-1-phenylpentafluoropropanes 4 . Alkenes 1 , where the para-substituent X H,Cl,and CF 3 give additionally 1,2-diethoxy-1-phenyltrifluoropropenes 5 and, where X = CF 3 also 2,2-diethoxy-1H-1-phenyltetrafluoropropane 6 . Overall regioselectivity of nucleophilic attack of the ethoxide ion on alkenes 1 exhibits the Hammett type correlation with O p values of substituents X: CH 3 O and CH 3 groups favour the attack on the vinylic carbon C-1, while CF 3 and Cl substituents direct the attack on the C-2 carbon of alkenes 1 . The E and Z isomers of 1-ethoxy and 1,2-diethoxy substituted alkenes 2 and 5 were formed in comparable amounts, while the E isomers of 2-ethoxy substituted alkenes 3 were always formed with a 93 – 97 % selectivity.