Add time:07/18/2019         Source:sciencedirect.com

Sodium dithionite initiated free-radical addition of polyfluoroalkyl iodides (2m–2s) with norbornene 1a and its derivatives, such as norbornene-2-carboxylates 1b and 1c, and norbornene-2-carboxylic acids 1d and 1e was investigated. In all the cases, the addition of RF group was stereoselectively delivered at exo-position and the predominant configuration of products was trans. Under the similar condition, norbornene-2-carboxylic ethyl ester 1b reacted with 2p to give 6-exo-RF-5-endo-iodo adduct 3bp and 5-exo-RF-6-endo-iodo adduct 5bp in the ratio of 4:1. While 1c, which has a heavy crowded group in the 2-endo-position, gave 6-exo-RF-5-endo-iodo adduct 3cp and polyfluoroalkylated product 4cp retaining the trans-configuration and the exo-orientation of RF group. The fluoroalkylation–lactonization reaction occurred in the reaction of norbornene-2-endo-carboxylic acids 1d and 1e with polyfluoroalkyl iodides to afford the corresponding fluoroalkylated γ-lactone products (7dp–7ds, and 7em–7er). The configuration of the products was further confirmed by 2D NMR and X-ray diffraction analyses for the first time.

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