The synthesis of aromatic divinylogs and aromatic halogenated vinylogs

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Abstract
Two new higher homologues of p‐divinylbenzene, p‐allylstyrene (p‐allylvinylbenzene) and p‐1‐propenylstyrene (p‐1‐propenylvinylbenzene) were synthesized and characterized. Intermediates for the synthesis of difunctional aromatic vinylogs, p‐chloro‐allylbenzene was prepared for the first time and p‐bromostyrene was made by methods different from those reported previously for this material. The usefulness of anhydrous cobaltous chloride for the activation of vinyl bromide in the reaction with aromatic Grignard compounds was demonstrated in the synthesis of p‐allyl‐ and p‐bromostyrene. Rearrangement of the allyl to the 1‐propenyl group on treatment with activated alumina at 300° was shown in the synthesis of p‐1‐propenylstyrene and 1‐propenylbenzene. Peroxide‐initiated bulk polymerization of p‐divinylbenzene, p‐1‐propenylstyrene, and p‐allylstyrene established the following order of reactivity: vinyl > 1‐propenyl > allyl. Preliminary polymerization of 1‐propenylstyrene and copolymerization with styrene in bulk and in solution showed the former to be an efficient though slower crosslinking agent than p‐divinylbenzene. Molding of solid copolymers of styrene and p‐1‐propenyl‐styrene was carried out, resulting in the formation of thermosetting clear and brittle resins.

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