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Abstract

A new methodology for the synthesis of a novel difunctional- and a known trifunctional initiator, i.e., 1,3-di(2-methoxy-2-propyl)-5-isopropyl benzene and 1,3,5-tri(2-methoxy-2-propyl)benzene, respectively, for the preparation of di- and tri-telechelic polyisobutylenes. The synthesis proceeds in three steps: 1) catalytic peroxidation of 1,3,5-triisopropylbenzene, 2) reduction of the peroxides to the corresponding alcohols, and 3) methylation of the alcohols. By controlling the conversion of the key peroxidation step the relative ratio of di- and tri-functional intermediates can be controlled. By the use of the 1,3-di(2-methoxy-2-propyl)-5-isopropyl-benzene, well-defined di-methoxy telechelic polyisobutylenes can be synthesized. Although the overall combined yield of the two initiators was only 14-20%, because of the low cost of the starting material, reagents used, and simple manipulations these compounds represent the most cost effective initiators to-date for the preparation of telechelic polyisobutylenes.

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