Silver-catalyzed rearrangement of propargylic sulfinates to allenic sulfones

被引：26

作者：

Harmata, Michael ^{[1
]}

Huang, Chaofeng ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 7-8期

关键词：

allenes; sigmatropic rearrangements; silver; sulfones;

D O I：

10.1002/adsc.200700447

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Treatment of propargylic sulfinate esters with 2 mol % of silver hexafluoroantimonate results in the rapid formation of allenic sulfones in essentially quantitative yield.

引用

页码：972 / 974

页数：3

共 61 条

[51] SYNTHESIS OF CYCLOPENTENYL SULFONES VIA THE [3 + 2] CYCLIZATION ELIMINATION-REACTION OF (PHENYLSULFONYL)ALLENE [J].

PADWA, A ;

YESKE, PE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1617-1618

[52] DIPOLAR CYCLOADDITION REACTIONS OF (PHENYLSULFONYL)ALKYNES AND (PHENYLSULFONYL)PROPADIENE WITH C,N-DIPHENYLNITRONE [J].

PARPANI, P ;

ZECCHI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1417-1421

[53]

Scheufler F, 2000, EUR J ORG CHEM, V2000, P3945

[54] Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: Efficient synthesis of heterocycles via cascade migration/cycloisomerization approach [J].

Schwier, Todd ;

Sromek, Anna W. ;

Yap, Dahrika M. L. ;

Chernyak, Dmitri ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) :9868-9878

[55] REARRANGEMENT OF AN ACETYLENIC SULPHINIC ESTER TO AN ALLENIC SULPHONE [J].

STIRLING, CJ .

CHEMICAL COMMUNICATIONS, 1967, (03) :131-&

[56] CYCLOAROMATIZATION AND DNA CLEAVAGE OF NOVEL ENYNE-ALLENE SYSTEMS [J].

TOSHIMA, K ;

OHTA, K ;

OHTSUKA, A ;

MATSUMURA, S ;

NAKATA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1406-1407

[57]

VANDERLINDEN JB, 1995, RECL TRAV CHIM PAY B, V114, P51

[58]

VENIARD L, 1973, B SOC CHIM FR II-CH, P2746

[59]

VENIARD L, 1968, CR ACAD SCI C CHIM, V266, P1092

[60] An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine [J].

Watanabe, Y ;

Mase, N ;

Tateyama, M ;

Toru, T .

TETRAHEDRON-ASYMMETRY, 1999, 10 (04) :737-745

← 1 2 3 4 5 6 7 →