DIELS-ALDER REACTIVITY OF VINYLSULFOXYALLENES

被引：12

作者：

WANG, XH

DONOVALOVA, J

HOLLIS, A

JOHNSON, D

RODRIGUEZ, A

KENNEDY, GD

KRISHNAN, G

BANKS, H

机构：

[1] GEORGIA STATE UNIV,LBCS,DEPT CHEM,ATLANTA,GA 30303

[2] USA,EDGEWOOD RES DEV,CTR ENGN,ABERDEEN PROVING GROUND,MD 21010

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1994年 / 31卷 / 04期

关键词：

D O I：

10.1002/jhet.5570310431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinylsulfoxyallenes 3a-c are prepared from propargylic alcohols in 47-65% yield. Vinylsulfoxyallenes undergo facile [4+2] cycloadditions with methyl triazolidenedione (MTAD) and singlet oxygen to afford phenylsulfinylpyridazines and spirocyclic phenylsulfinyl-2H-pyran-3(6H)-ones in excellent yields (60-90%). Spirocyclic phenylsulfinyl-2H-pyran-3(6H)-ones are oxidized to the corresponding phenylsulfones with peracid or can be epoxidized with basic hydrogen peroxide. Spirocyclic pyranone formation is thought to proceed via the rearrangement of a labile cyclic peroxide intermediate 14.

引用

收藏

页码：871 / 876

页数：6

相关论文

共 37 条

[1] THE SYNTHESIS OF UNUSUAL ORGANIC-MOLECULES FROM AZOALKANES [J].

ADAM, W ;

DELUCCHI, O .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (10) :762-779

[2] HOW MECHANISTICALLY EQUIVALENT ARE SINGLET OXYGEN AND TRIAZOLINEDIONE - REGIOCHEMICAL AND STEREOCHEMICAL DIFFERENCES IN THEIR ENE REACTIONS WITH ALLYLSILANES [J].

ADAM, W ;

SCHWARM, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :3129-3130

[3] REACTION OF SINGLET OXYGEN WITH ALKENYLIDENECYCLOPROPANES - IMPLICATION FOR A PEROXYALLYL INTERMEDIATE [J].

AKASAKA, T ;

MISAWA, Y ;

ANDO, W .

TETRAHEDRON LETTERS, 1990, 31 (08) :1173-1176

[4] STEREOSELECTIVE SYNTHESIS OF BOTH (E)-1,2,4-HEPTATRIEN-6-YNES AND (Z)-1,2,4-HEPTATRIEN-6-YNES - FORMATION OF AN ALPHA,3-DEHYDROTOLUENE BIRADICAL, TRAPPING BY AN INTRAMOLECULAR CARBON CARBON DOUBLE-BOND, AND DECAY OF THE RESULTING NEW BIRADICAL VIA AN INTRAMOLECULAR ROUTE [J].

ANDEMICHAEL, YW ;

GU, YG ;

WANG, KK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :794-796

[5] 6-MEMBERED RING-FUSED THIIRENE S-OXIDES - SYNTHESIS, CHARACTERIZATION, AND REACTIVITY [J].

ANDO, W ;

HANYU, Y ;

TAKATA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11) :2122-2125

[6] SPONTANEOUS AROMATIZATION OF DIELS-ALDER ADDUCTS IN THE REACTION OF ALKATRIENYLPHOSPHONATES WITH DIALKYL ESTERS OF ACETYLENEDICARBOXYLIC ACID [J].

ANGELOV, CM ;

MONDESHKA, DM ;

TANCHEVA, TN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) :647-648

[7]

BERTRAND M, 1971, B SOC CHIM FR, P962

[8] PALLADIUM-CATALYZED SYNTHESIS OF NEW UNSATURATED EXO-ENOL LACTONES WITH POTENTIAL BIOLOGICAL-ACTIVITY [J].

BOUYSSI, D ;

GORE, J ;

BALME, G ;

LOUIS, D ;

WALLACH, J .

TETRAHEDRON LETTERS, 1993, 34 (19) :3129-3130

[9]

Carruthers W., 1990, TETRAHEDRON ORGANIC, V8

[10] REACTION OF ELECTROPHILES WITH UNSATURATED SYSTEMS - TRIAZOLINEDIONE-OLEFIN REACTIONS [J].

CHENG, CC ;

SEYMOUR, CA ;

PETTI, MA ;

GREENE, FD ;

BLOUNT, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) :2910-2916

← 1 2 3 4 →