Reaction of Perfluoroalkanesulfinates with Allyl and Propargyl Halides. A Convenient Synthesis of 3-(Perfluoroalkyl)prop-1-enes and 3-(Perfluoroalkyl)allenes

DOI: 10.1021/jo00008a041

Source and publish data:

Journal of Organic Chemistry p. 2801 - 2804 (1991)

Update date:2022-08-04

Topics:

Authors:

Hu, Chang-Ming

Qing, Feng-Ling

Huang, Wei-Yuan

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Article abstract of DOI:10.1021/jo00008a041

The reaction of perfluoroalkanesulfinates, R_fCF2SO2Na, with allyl and propargyl halides, in the presence of (NH4)2S2O8, gave 3-(perfluoroalkyl)prop-1-enes (R_fCH2CH=CH2) and 3-(perfluoroalkyl)allenes (R_fCH=C=CH2), respectively, in good yield.Evidence is presented for a radical addition-elimination mechanism for the reaction.The reaction represents a synthetically viable and convenient route to such compounds.

Full text of DOI:10.1021/jo00008a041

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