Tetrahedron p. 4661 - 4670 (1986)
Update date:2022-07-30
Topics:
Chan, Tze-Ming
Friary, R.
Pramanik, B.
Puar, M. S.
Seidl, V.
Mc Phail, Andrew T.
N-oxidation of 2-methyl-3β-phenyl-2,3α,3aβ,6aβ-tetrahydrothieno<2,3-d>isoxazole-4,4-dioxide (1) gave a nitrone (2) which underwent an intramolecular 1,3-dipolar cycloaddition yielding a tricyclic isoxazolidine (4).A single-crystal X-ray analysis unequivocally established the structure of 4 as 9β-phenyl-2-oxa-6-thia-1-azatricyclo<3.3.1.O3,7>nonan-4α-ol-6,6-dioxide.LiAlH4 and LiAlD4 reduced 4 exhaustively and rearranged it profoundly to isotopomers 5 and 6, respectively; a novel Grob fragmentation may have mediated the rearrangement.Inter alia, measurements of 13C-13C coupling constants and of m/z ratios of fragment ions yielded the complete structures of 5 and 6.They are 5β-phenyl-8-thia-6-azabicyclo<3.3.1>octan-2α-ol and its 3α-deuterio analog, respectively.
View MoreDayang Chem (Hangzhou) Co.,Ltd.
website:http://www.dycnchem.com
Contact:+86-571-88938639
Address:9/F, Unit 2 Changdi Torch Building, 259# WenSan Road, Xihu District, Hangzhou City 310012, P.R.China
Nantong Kaixin Pharma Chemical Co.,Ltd.
Contact:86-513-85250786
Address:2-1103 Huachen Mansion, 111 Gongnong Road,Nantong, Jiangsu, China
LIAOYANG WANRONG CHEMICALS COMPANY LIMITED
Contact:86-419-2390789
Address:XINLI VILLAGE , DONG NINGWEI COUNTY,TAIZIHE DISTRICT, LIAOYANG , LIAONING
Changsha Huajing Powdery Material Technological Co., Ltd.
Contact:86-731-88879686
Address:Building 2, West Garden, Main Campus of Central South University, Changsha, Hunan Province, China
jiangsu hualin chemical co.,ltd.
Contact:86-25-87787402
Address:jaingsu,china
Doi:10.3184/030823408X298508
(2008)Doi:10.1021/jm800787b
(2008)Doi:10.1016/j.bmcl.2008.10.096
(2009)Doi:10.1016/j.tetlet.2006.05.173
(2006)Doi:10.1007/s10600-006-0060-3
(2006)Doi:10.1016/j.ica.2005.11.007
(2006)
