Tetrahedron p. 75 - 83 (1982)
Update date:2022-08-05
Topics:
Sasaki, Tadashi
Hayakawa, Kenji
Nishida, Sumio
Photochemistry of α,α-bisulfenylated ketone has been investigated.Irradiation of 2-phenylthiodihydrothiophen-3-one (1) in benzene gave the radical recombination products 9 (63percent) and 10 (49percent).In a polar solvent, the ionic chemistry became predominant.Brief irradiation of 1 in acetonitrile and methanol gave the cis-fused dihydrothiophene 11 as the major product in 43percent and 20percent yields, respectively.The stereoselective photocyclization was generally observed for other ketones (2-8) in acetonitrile solution (Table 1).The photoproducts were easily dehydrated by treating with boron trifluoride etherate to give the corresponding benzothiophenes in high yields.Simple α-phenylthioketones are photoinert under the same conditions.The mechanism of this novel photocyclization of bisulfenylated ketones is also discussed.
View MoreDalian Join King Biochemical Tech. Co., Ltd.
Contact:0411 39216206
Address:814 First State Blvd
Contact:+86-25-52346955
Address:199,JIANYE ROAD,NANJING,CHINA
ShangHai Soyoung Biotechnology Inc
website:http://www.soyoungbio.com
Contact:+86-21-69893009
Address:shanghai
Contact:+86-512-69561895
Address:No.111, Building A4, 218 Xinghu Street, Suzhou Industrial Park, P. R. China
Hebei Fulong Import & Export Co., Ltd.
Contact:86-311-87795661
Address:15A19 Zhongyuan Building,368 Youyi North Street,Shijiazhuang 050070,China
Doi:10.1016/S0040-4039(00)93674-8
(1980)Doi:10.1039/DT9810000463
(1981)Doi:10.1016/0040-4039(80)80104-3
(1980)Doi:10.1021/ja910290c
(2010)Doi:10.1039/b9nj00255c
(2009)Doi:10.1248/cpb.29.558
(1981)