Synthesis and Isolation of 1-Cyclohex-1,2-dien-1-ylbenzene from 1-(2-Iodocyclohex-1-en-1-yl)benzene and 1-(2-Iodocyclohex-2-en-1-yl)benzene

Authors : Mustafa CEYLAN, Yakup BUDAK, M. Burcu GÜRDERE

Pages : 647-657

View : 9 | Download : 5

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :The key compounds, 1-insert ignore into journalissuearticles values(2-iodocyclohex-1-en-1-yl); benzene insert ignore into journalissuearticles values(12); and 1-insert ignore into journalissuearticles values(2-iodocyclohex-2-en-1-yl); benzene insert ignore into journalissuearticles values(13);, for the generation of 1-cyclohex-1,2-dien-1-ylbezene insert ignore into journalissuearticles values(20); were synthesized starting with cyclohexanone. Separate reactions of 12 and 13 with KOtBu in benzene in a sealed tube at 180 °C gave 6 products: 1-cyclohex-1-en-1-ylbenzene insert ignore into journalissuearticles values(8);, 2-phenylcyclohexanone insert ignore into journalissuearticles values(10);, 1,8-diphenyl-2,3,4,4a,4b,5,6,7-octahydrobiphenylene insert ignore into journalissuearticles values(21);, 8a-phenyl-1,2,3,4,6,7,8,8a-octahyd-rotriphenylene insert ignore into journalissuearticles values(22);, 1,2-diphenylcyclohexene insert ignore into journalissuearticles values(23);, and 1-insert ignore into journalissuearticles values(2-tert-butoxycyclohex-1-enyl); benzene insert ignore into journalissuearticles values(24);. In addition, reactions of 12 and 13 under the same conditions in the presence of diphenylisobenzofuran and furan as trapping reagents afforded the [4 + 2] cyclo-adducts 30, 31, and 32 in good yields, respectively.
Keywords : Cyclic strained allenes, dehydroiodination, dimerisation, cycloaddition