Tetrahedron p. 12395 - 12406 (1994)
Update date:2022-07-29
Topics:
Benati, Luisa
Capella, Laura
Montevecchi, Pier Carlo
Spagnolo, Piero
Phenylsulfenocyclization of a number of alkenes and alkynes possessing internal hydroxyl, carboxyl or vinyl functionality has been investigated with NBSA. Thioetherification of 4-penten-1-ol 4 as well as thiolactonization of 4-penten-1-oic acid 7 and, to a modest extent, 4-pentyn-1-oic acid 8 can be successfully achieved with NBSA in the presence of boron trifluoride. On the other hand, under analogous conditions 3-buten-1-ol 3 and 3-buten-1-oic acid 6 fail to undergo thiocyclization and give instead oxa- and/or aza-sulfenylation 1,2-adducts. Similar failure is observed with 4-pentyn-1-ol 5, in which case diphenyl disulfide and 4-nitroaniline are the exclusive products. Hexa-1,5-diene 9, to some extent, affords a cyclized arylaminosulfide, i.e. 23, ascribable to formal loss of a methylene unit from the initial (phenylthiomethyl)- cyclopentyl cation 24. The reaction products are discussed in terms of intermediate thiiranium and thiirenium ions whose decomposition mode is strictly dependent upon their structural features. Novel evidence is also presented that aluminium chloride and bromide can promote reaction of NBSA with alkenes and alkynes to afford chloro- and bromo-sulfenylation adducts in varying yields.
View MoreShanghai Pinewood Fine Chemical Co., Ltd.
website:http://www.pinewoodchem.com
Contact:0086-21-62417129,62414096
Address:Suite B, 27F, No.2, Lane 600, Tianshan Road, Shanghai
SJZ Chenghui Chemical Co., Ltd.
Contact:86-311-87713916
Address:no.368 youyi north avenue
Contact:+86-25-8776 0031
Address:3-2001 Jiaye Int'l Town, 158 Lushan Road,Nanjing, 210019, China
Contact:86-15588110016
Address:LINYI CITY,SHANDONG PROVINCE,CHINA
JIANGXI AIFEIMU TECHNOLOGY CO.,LTD
Contact:+86-570-6040289
Address:FINECHEMICAL PARK,ZIBU TOWN,WANNIAN COUNTY,JIANGXI PROV.,CHINA,ZIP
Doi:10.1055/s-1975-23658
(1975)Doi:10.1039/c5sc04590h
(2016)Doi:10.1021/jo00900a031
(1975)Doi:10.1007/BF00905308
()Doi:10.1021/ja01047a015
(1969)Doi:10.1002/oms.1210030907
(1970)