The Polymerization of Indene, Cinnamal Fluorene and Some Derivatives of Indene

Abstract

Vol. 50 chloride. The methylcreatinine hydrochloride thus obtained melted with slight decomposition at 234-236°, as reported. All attempts to condense this product with benzaldehyde, either by the usual procedure or with longer heating and increased proportions of sodium acetate and of acetic anhydride, were completely unsuccessful.At this stage it was thought worth while to show that the methylation could not have taken place with the introduction of a second methyl group on the 1-nitrogen.The methylcreatinine was accordingly hydrolyzed and found to yield sarcosine and methylamine. Since it was thus clear that the substance must have one of the two structures represented by VIII and IX, it was sought to convert it into a mixture of these two isomers (see discussion) in the hope that at least one of them might be condensed with benzaldehyde. The mixture obtained, however, gave no benzal derivative.

Polymerization.

“…It has already been mentioned that the first step in the polymerization of ethylene is the formation of butene-1 and the second step is the formation of hexene-1. Similar terminal unsaturations have been found by Whitby and Katz in a still longer series of polyindenes, and this suggests that the most plausible mechanism for the polymerization of vinyl compounds is "best represented as proceeding stepwise by the addition regularly of successive molecules of monomer to the double bond present at each stage of the polymerization immediately preceding" (105). This mechanism may be formulated as follows:…”

“…CH*=CH-COOH Acrylic acid (99) CH*=CH-CHO Acrolein (100) Indene (101, 105) The most extensive and important studies of the polymeriaation of vinyl compounds are those carried out by Staudinger and his coworkers. CH*=CH-COOH Acrylic acid (99) CH*=CH-CHO Acrolein (100) Indene (101, 105) The most extensive and important studies of the polymeriaation of vinyl compounds are those carried out by Staudinger and his coworkers.…”

“…Although the composition of this hydrocarbon does not exactly correspond to that required by the expected structure for the polymerization of vinyl compounds is "best represented as proceeding stepwise by the addition regularly of successive molecules of monomer to the double bond present at each stage of the polymerization immediately preceding" (105). Although the composition of this hydrocarbon does not exactly correspond to that required by the expected structure for the polymerization of vinyl compounds is "best represented as proceeding stepwise by the addition regularly of successive molecules of monomer to the double bond present at each stage of the polymerization immediately preceding" (105).…”

The Fractionation of High-Polymeric Substances.

“…In 1928, Whitby and Katz (300) studied the polymerization of indene, cinnamalfluorene, and cinnamalindene. They demonstrated the heterogeneity of the products by fractional precipitation, using benzene as the solvent and alcohol as the precipitant; polyindene yielded seven fractions, polycinnamalfluorene five, and polycinnamalindene four.…”

Thermal Reactions of Terpene Hydrocarbons.

“…Whitby and Katz (190) have suggested that the most plausible mechanism for the polymerization of unsaturated compounds is "best represented as proceeding stepwise by the addition regularly of successive molecules of monomer to the double bond present at each stage of the polymerization immediately preceding." This, of course, applies to any olefinic compound.…”