Rearrangement of 2-iodo-3-perfluoroalkyl-1-propyl acetates to 1-iodo-3-perfluoroalkyl-2-propyl acetates

Add time:08/20/2019    Source:sciencedirect.com

2-Iodo-3-perfluoroalkylpropyl acetates, RFCH2CHICH2OAc (1) (RF = i-C3F7, C4F9, C6F13, C8F17), have been rearranged thermally to 1-iodo-3-perfluoroalkyl-2-propyl acetates, RFCH2CH(OAc)CH2I (2), in 89% yield over the temperature range 120–200 °C. The results indicate that the rearrangement is a reversible process which is shifted towards the formation of 2. The equilibrium regio isomer ratio (12 = 1:8) was independent of the temperature and of the nature of the RF substituent. It is proposed that the rearrangement proceeds through a free-radical mechanism including 1,2-migration of the acetoxy group after thermal scission of the CI bond.

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