Department of Chemistry, Stony Brook University , Stony Brook, New York 11794-3400, United States.
J Org Chem. 2018 Mar 2;83(5):2892-2897. doi: 10.1021/acs.joc.8b00054. Epub 2018 Feb 14.
Bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides undergo alternating ring-opening metathesis polymerization (AROMP) with cyclohexene. Herein, a general method for the preparation of bicyclo[4.2.0]oct-(8)-ene-8-carboxy derivatives is described. The central 8-cyano intermediate provides entry to five different functional group substituents on the alkene. These monomers were tested as potential substrates for AROMP with cyclohexene. In addition to the carboxamide, the carboxynitrile and carboxaldehyde are also substrates for AROMP. In the case of the carboxaldehyde, the polymer is regioregular. However, the addition of carboxynitrile is stereoirregular and slow.
双环[4.2.0]辛-1(8)-烯-8-甲酰胺与环已烯进行交替开环复分解聚合(AROMP)。本文描述了一种制备双环[4.2.0]辛-(8)-烯-8-羧酸衍生物的通用方法。中间的 8-氰基中间体为烯烃上的 5 种不同官能团取代基提供了入口。这些单体被测试为与环已烯进行 AROMP 的潜在底物。除了酰胺外,氰基羧酸和醛也是 AROMP 的底物。对于醛,聚合物是区域规整的。然而,氰基羧酸的加成是立体不规则且缓慢的。