Journal of Organic Chemistry p. 921 - 927 (1991)
Update date:2022-09-26
Topics:
Omura, Kanji
Dimer 3 dissociates in solution to give the phenoxy radical 4.When solid 3 is dissolved in a solution of phenol 11a, radical 4 dehydrogenates the phenol to afford phenol 5 and phenoxy radical 12.Radical 12 couples with more 4 to afford principally bis(cyclohexadienone) 16a and a minor amount of the dimeric bis(cyclohexadienone) 13.The preferential formation of 16a over 13 is explained as the result of a solvent-cage reaction.Compounds 13 and 16a are isomerized in the presence of silica gel or triethylamine to 4,4'-dihydroxybiphenyl 14 and phenolic dienone 17a, respectively.Compound 13 is relatively stable in hexane at 30 deg C, while 16a slowly dissociates under these conditions to afford parent radicals 4 and 12.If 11a is present, radical 4 either recombines with 12 or dehydrogenates the phenol.Two radicals of 12 generated by the dissociation of 16a and the subsequent dehydrogenation of 11a couple to give 13.Therefore, dissolving 3 in hexane containing excess 11a and keeping the resulting solution at 30 deg C results in the preferential formation of 13.Dissolving 3 in triethylamine containing phenols 11 or 21 similarly affords dienones 17 or 23.The yields of these dienones increase with increasing electron-donating capability of the substituent of the phenol ring.
View MoreChengda Pharmaceuticals Co., Ltd.
Contact:+86-573-84601188
Address:hengshan Road 5# in Jiashan, zhejiang
Jiangsu Chunjiang AgroChemical Co.,Ltd.
Contact:+86-13817348163
Address:Panjiawan 84, Zhixi Town, Jintan City, China
Shanghai Zhihua ChemTech Co., Ltd.
Contact:+86-13774313779
Address:Room 817 Suite B 3333 Shenjiang Road
Contact:13813902930 025-52714267
Address:20 Fengji Road, Yuhua Economic Development Zone, Nanjing, Jiangsu, P. R. China
Jiangxi Lixin Pharmaceutical Co.,Ltd.
Contact:0798-8337222; 18979813215
Address:Jiangxi City, Jindezheng Province
Doi:10.14233/ajchem.2015.18532
(2015)Doi:10.1002/anie.201711535
(2018)Doi:10.1021/co2001058
(2011)Doi:10.1007/BF02128127
(1985)Doi:10.1080/00397911.2010.515361
(2011)Doi:10.1055/s-2006-951550
(2006)