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of patents on such polymerization of olefinic compounds have appeared. In continuing the theoretical studies8 of olefin polymerization in this Laboratory, we have been led to investigate the action of boron trifluoride on alcohols, a type of reaction which has not been reported previously. This is of particular interest since this halide is believed to yield true polymerization products by its action on isobutylene at low temperatures.4We have found that the action of boron trifluoride on isopropyl alcohol proceeds with the formation of polymerized products and from the reaction mixture we have isolated substantial yields of tetrapropylene.Boron trifluoride (1400 g.) was dissolved in 2 kg. of isopropyl alcohol with external cooling and the resulting solution was heated in a loosely-(3) Whitmore, Ini. Eng. Chem., 26, 94 (1934). (4) I. G. Farbenindustrie, British Patent 401,297.

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procedure, are summarized in Table X. There is some indication that the n-propylamine used to prepare the 1-diazopropane was not entirely pure, which may account in part for the lower yields and less pure products in this series. SUMMARY 1. Procedures have been developed which make it possible to use the Amdt-Eistert reaction with higher diazohydrocarbons.2. The reaction has been employed with diazoethane and 1-diazopropane to prepare -methyl and -ethyl homologs, respectively, of the starting acid.3. An improved method for effecting rearrangement of the diazoketones was developed, involving heating at 180-190°with benzyl alcohol and a tertiary amine.Madison 6, Wis.

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