An α,α′-dioxothione and its [4+2] cycloaddition with trans-cyclooctene in the reaction of ninhydrin with potassium thiotosylate

被引：11

作者：

Adam, W ^{[1
]}

Fröhling, B ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol000154j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] In the reaction of Ninhydrin (1a)/1,2,3 indantrione (1b) with potassium thiotosylate, 1,4-oxathiin 6 is formed in up to 63% yield as the trapping product of the intermediary alpha,alpha'-dioxothione 1c with trans-cyclooctene (3a). Additionally, up to 18% of the available sulfur is transferred to olefin 3a to thiirane 3b through the intermediary oxathiirane.

引用

页码：2519 / 2522

页数：4

共 15 条

[1] Direct thioepoxidation of strained cyclic alkenes by the photolytic sulfur-atom transfer from thiocarbonyl S-oxides (sulfines)
Adam, W
Deeg, O
Weinkotz, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7084 - 7085
[2] BEELITZ K, 1978, Z NATURFORSCH B, V33, P417
[3] alpha,alpha'-dioxothiones .2. Asymmetric Diels-Alder reactions of chiral non-racemic alpha,alpha'-dioxothiones
Boccardo, G
Capozzi, G
Giuntini, M
Menichetti, S
Nativi, C
[J]. TETRAHEDRON, 1997, 53 (51) : 17383 - 17394
[4] PHTHALIMIDOSULFENYL CHLORIDE .5. REACTION WITH ENOLIZABLE CARBONYL-COMPOUNDS AND SYNTHESIS OF FUNCTIONALIZED THIONES
CAPOZZI, G
MENICHETTI, S
NATIVI, C
ROSI, A
VALLE, G
[J]. TETRAHEDRON, 1992, 48 (41) : 9023 - 9032
[5] PHTHALIMIDESULFENYL CHLORIDE .9. A SIMPLE ACCESS TO ALPHA,ALPHA'-DIOXOTHIONES, A NEW CLASS OF BIS-HETERODIENES - SYNTHESIS OF 1,4-OXATHIIN SYSTEMS
CAPOZZI, G
FRANCK, RW
MATTIOLI, M
MENICHETTI, S
NATIVI, C
VALLE, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) : 6416 - 6426
[6] OXATHIIRANS AS INTERMEDIATES IN PHOTOLYSIS OF SULFINES
CARLSEN, L
HARRIT, N
HOLM, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (13): : 1404 - 1407
[7] ORGANOPHOSPHORUS COMPOUNDS REACTION OF THIOPHENOLS AND THIOL ACIDS WITH BENZILMONOANILS
HAFEZ, TS
ZAYED, MF
FAHMY, AA
ISMAIL, NA
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 56 (1-4): : 231 - 235
[8] THIATION REACTIONS OF SOME ACTIVE CARBONYL-COMPOUNDS WITH SULFUR TRANSFER REAGENTS
HUANG, NZ
LAKSHMIKANTHAM, MV
CAVA, MP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) : 169 - 172
[9] OXATHIIRANES .9. AN ABINITIO CASSCF STUDY OF THE PHOTOLYTICAL FORMATION AND DECOMPOSITION OF OXATHIIRANE
KARLSTROM, G
ROOS, BO
CARLSEN, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) : 1557 - 1561
[10] Structure and conformation of cyclopentene, cycloheptene and trans-cyclooctene
Leong, MK
Mastryukov, VS
Boggs, JE
[J]. JOURNAL OF MOLECULAR STRUCTURE, 1998, 445 (1-3) : 149 - 160

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