Journal of Organic Chemistry p. 4157 - 4161 (1981)
Update date:2022-08-05
Topics:
McCourt, David W.
Roller, Peter P.
Gelboin Harry V.
Vicinal dihydro diols of benzopyrene and benzanthracene are dehydrated to their phenolic derivatives by the methanol eluate of reverse-phase (octadecylsilane) columns previously treated with tetrabutylammonium phosphate.Phenols are also produced by treating the dihydro diols with methanolic tetrabutylammonium hydroxide on removal solvent.In most cases the regioselectivity is markedly different from the acid-catalyzed dehydration.The in situ generated tetrabutylammonium phenoxides are converted to the butyl ethers at high temperatures (150 deg C) but not under th e conditions of dehydration (60 deg C).Tetraethylammonium and tetramethylammonium hydroxides also dehydrate dihydro diols, whereas potassium and sodium hydroxides do not.Dehydration does occur by treatment of dihydro diols with potassium hydroxide in the presence of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) and with sodium methoxide in the presence of tetrabutylammonium chloride.A mechanism is suggested.
View MoreEngineering Research Center of Pesticide, Heilongjiang Province
Contact:+86-451-86609001
Address:No.74 of Xuefu Road, Nangang District,
Hangzhou TJM Chemical Trade Co., Ltd
Contact:86-571-88223276 86-13388481653
Address:2221#,Boyuexuan,1860# Binsheng Road,Binjiang District, Hangzhou CityZhejiang Province, 310051, P. R. China
Contact:86-28-61993785
Address:No.70-13-21, North Section, Erhuan
Contact:86 513 85512619
Address:Rm.1306, Building A, Wenfeng Mansion,168 Gongnong Road, Nantong Jiangsu China
website:http://www.apeptides.com/en/
Contact:+86-21-60871011
Address:No. 80 Chuanshan Shuyuan Steet,Pudong,Shanghai
Doi:10.1055/s-2001-12352
(2001)Doi:10.1016/S0040-4039(00)84813-3
(1986)Doi:10.1002/1099-0690(200104)2001:7<1407::aid-ejoc1407>3.0.co;2-n
(2001)Doi:10.1039/d0gc02372h
(2020)Doi:10.1021/ja01148a525
(1951)Doi:10.1021/ol015938r
(2001)
