Generation of allenylthioketene S,S-dioxides through [3,3] sigmatropic rearrangement of alkynyl propargyl sulfones

被引：8

作者：

Aoyagi, Shigenobu ^{[1
]}

Koyanagi, Makoto ^{[1
]}

Takahashi, Megumi ^{[1
]}

Shimada, Kazuaki ^{[1
]}

Takikawa, Yuji ^{[1
]}

机构：

[1] Iwate Univ, Fac Engn, Dept Chem Engn, Morioka, Iwate 0208551, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 11期

关键词：

D O I：

10.1016/j.tetlet.2007.01.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thioketene S,S-dioxides 2 were successfully generated through [3,3] sigmatropic rearrangement of alkynyl propargy] sulfones 1 and the formation of 2 was confirmed by trapping experiment using cyclohexene or allyltrimethylsilane affording a [2+2] cycloadduct 5. In situ generated thioketene S,S-dioxides 2 underwent facile conversion into allenynes 3 in moderate yields, via formation and subsequent [1,2] shift of vinylidene carbenes. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1915 / 1918

页数：4

共 31 条

[1] Synthesis of δ-thiolactams by the aza-Diels-Alder reaction of in situ generated allenyltrimethylsilylthioketenes with imines [J].

Aoyagi, Shigenobu ;

Hakoishi, Michiko ;

Suzuki, Mariko ;

Nakanoya, Yusuke ;

Shimada, Kazuaki ;

Takikawa, Yuji .

TETRAHEDRON LETTERS, 2006, 47 (44) :7763-7766

[2] Isolation and characterization of an allenylthioketene and 4-methylenecyclobutenethiones generated by thermal reaction of alkynyl propargyl sulfides [J].

Aoyagi, Shigenobu ;

Sugimura, Katsuaki ;

Kanno, Nobuya ;

Watanabe, Dai ;

Shimada, Kazuaki ;

Takikawa, Yuji .

CHEMISTRY LETTERS, 2006, 35 (09) :992-993

[3] THE CHEMISTRY OF SULFINES .12. UNUSUALLY FACILE THIO-CLAISEN REARRANGEMENT OF 1-ALKENYL 2-ALKENYL SULFOXIDES - A NEW SULFINE SYNTHESIS [J].

BLOCK, E ;

AHMAD, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (23) :6731-6732

[4] REACTION OF STEREOISOMERIC C-14-LABELED 1-BROMO-2,2-DIARYLETHYLENES AND BETA-BROMOSTYRENES WITH BUTYLLITHIUM [J].

CURTIN, DY ;

FLYNN, EW ;

NYSTROM, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) :4599-4601

[5] DI-T-BUTYLTHIOKETENE [J].

ELAM, EU ;

RASH, FH ;

DOUGHERT.JT ;

GOODLETT, VW ;

BRANNOCK, KC .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (07) :2738-&

[6] REARRANGEMENT OF BROMOMETHYLENECYCLOALKANES WITH POTASSIUM T-BUTOXIDE [J].

ERICKSON, KL ;

WOLINSKY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (05) :1142-&

[7]

Fischer N H, 1970, SYNTHESIS-STUTTGART, P393

[8] INTRAMOLECULAR CARBON-HYDROGEN INSERTIONS OF ALKYLIDENECARBENES .1. SELECTIVITY [J].

GILBERT, JC ;

GIAMALVA, DH ;

WEERASOORIYA, U .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5251-5256

[9]

GUEUGNOT SC, 2000, TETRAHEDRON, V56, P1851

[10] Generation of cycloalkylidene carbenes via exo-type cyclization of alkynyllithiums bearing remote leaving group [J].

Harada, T ;

Iwazaki, K ;

Otani, T ;

Oku, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9007-9012

← 1 2 3 4 →