Add time:08/17/2019         Source:sciencedirect.com

Reactions of CF3CF2CFCCl2 (1) with various nucleophiles such as MeO−, PhO−, NH3, n-c4H9MgBr and n-C4H9S− were studied. Contrary to a prior report [3], the addition is bidirectional and except for Pho−, nucleophiles would rather attack the CF site (path 1) than the CCL2 site (path 2), no matter whether the base is soft or hard. PhO− attacked both sites at nearly 1:1 ratio. Temperature had little effect on the direction of Meo− attack, but solvents could change its reaction rate and the distribution of products. Compared with CF2CFCF2CFCFCl2 (2) and CF3CFCFCFCl2 (trans, 3), preliminary experiments indicated that the order of reactivity increases along with the series of 1<3<2.

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