PREPARATION AND REARRANGEMENT OF 2-ALLYLOXYETHYL ARYL SULFOXIDES - A MERCURY-FREE CLAISEN SEQUENCE

被引：31

作者：

MANDAI, T ^{[1
]}

UEDA, M ^{[1
]}

HASEGAWA, S ^{[1
]}

KAWADA, M ^{[1
]}

TSUJI, J ^{[1
]}

SAITO, S ^{[1
]}

机构：

[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(00)94494-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkali metal hydride promoted addition of allylic alcohols to aryl vinyl sulfoxides at room temperature gives 2-allyloxyethyl aryl sulfoxides, which, on heating, are converted into γ,δ-unsaturated aldehydes via allylic vinyl ethers. © 1990.

引用

页码：4041 / 4044

页数：4

共 8 条

[1]

BUCHI G, 1983, J ORG CHEM, V48, P5406

[2] A NEW AND FACILE ROUTE TO SPIRO-KETAL SKELETON VIA HIGHLY STEREOSELECTIVE C-O BOND FORMATION BY INTRAMOLECULAR MICHAEL ADDITION TO ALPHA,BETA-UNSATURATED SULFOXIDES [J].

IWATA, C ;

HATTORI, K ;

UCHIDA, S ;

IMANISHI, T .

TETRAHEDRON LETTERS, 1984, 25 (28) :2995-2998

[3] INTRAMOLECULAR MICHAEL ADDITION-REACTION TO CHIRAL VINYLIC SULFOXIDES - AN ENANTIOSELECTIVE SYNTHESIS OF (R)-1,7-DIOXASPIRO[5.5]UNDECANE AND (S)-1,7-DIOXASPIRO[5.5]UNDECANE [J].

IWATA, C ;

FUJITA, M ;

HATTORI, K ;

UCHIDA, S ;

IMANISHI, T .

TETRAHEDRON LETTERS, 1985, 26 (18) :2221-2224

[4] MODELING CHEMICAL-REACTIVITY .3. STEREOCHEMISTRY OF MICHAEL ADDITIONS OF VINYL SULFOXIDES [J].

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7399-7400

[5] APPLICATIONS OF ORGANOFLUORINE REAGENTS IN GENERAL ORGANIC-SYNTHESIS .9. - SYNTHETIC UTILITY OF A FLUORINE-FACILITATED CLAISEN REARRANGEMENT - A NOVEL SYNTHETIC METHOD FOR 2,4-ALKADIENOIC ACIDS USING 2,2,2-TRIFLUOROETHYL PHENYL SULFOXIDE [J].

NAKAI, T ;

TANAKA, K ;

OGASAWARA, K ;

ISHIKAWA, N .

CHEMISTRY LETTERS, 1981, (09) :1289-1292

[6] APPLICATION OF CHIRAL SULFOXIDES IN ASYMMETRIC-SYNTHESIS - THE ENANTIOSPECIFIC SYNTHESIS OF THE CHROMAN RING OF ALPHA-TOCOPHEROL (VITAMIN-E) [J].

SOLLADIE, G ;

MOINE, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (20) :6097-6098

[7]

VOGEL DE, 1987, ORG SYNTH, V66, P29

[8] THE THERMAL, ALIPHATIC CLAISEN REARRANGEMENT [J].

ZIEGLER, FE .

CHEMICAL REVIEWS, 1988, 88 (08) :1423-1452

← 1 →