CONFIGURATIONALLY AND CONFORMATIONALLY HOMOGENEOUS CYCLIC N-ARYL SULFIMIDES .3. STEREOCHEMISTRY OF REARRANGEMENT

被引：8

作者：

CLAUS, PK

RIEDER, W

VIERHAPPER, FW

BAILER, J

机构：

[1] Institut für Organische Chemie der Universität Wien, A-1090 Wien

来源：

TETRAHEDRON | 1979年 / 35卷 / 11期

关键词：

D O I：

10.1016/0040-4020(79)85031-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Configurationally and conformationally homogeneous thiane- and trans- and cis-1-thiadecalin-1-N-p-chlorophenyl imides were rearranged to the corresponding 2-(2'-amino-5'-chlorophenyl)-sulfides and the configurations of the products were assigned by 1H-NMR spectroscopy. If sterically unhindered, rearrangements proceeded with a high degree (95%) of stereospecifity: sulfimides with equatorial S-N-bond gave rearranged products with axial, sulfimides with axial S-N-bond gave rearranged products with equatorial aryl substituent. The proposed concerted mechanism via a cyclic transition state is supported by these results. © 1979.

引用

页码：1373 / 1383

页数：11

共 50 条

[31] MOLECULAR REARRANGEMENTS .3. THE THERMAL REARRANGEMENT OF ARYL BENZYL ETHERS [J].

ELKOBAISI, FM ;

HICKINBOTTOM, WJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAY) :1873-1876

[32] Rearrangement of allyl aryl ethers .3. Reaction of alkoxyhydroquinone with cycloalkenediols [J].

Novak, L ;

Kovacs, P ;

Pirok, G ;

Kolonits, P ;

Hanania, M ;

Donath, K ;

Szantay, C .

TETRAHEDRON, 1997, 53 (28) :9789-9798

[33] ORTHO-FORMYLATION OF ANILINES BY REARRANGEMENT OF BIS(METHYLTHIO)METHANE-S-(N-ARYL)IMIDES [J].

CLAUS, PK ;

JAGER, E ;

SETZER, A .

MONATSHEFTE FUR CHEMIE, 1985, 116 (8-9) :1017-1026

[34] ORTHO-CLAISEN REARRANGEMENT .3. REARRANGEMENT OF BETA-ALKYLALLY ARYL ETHERS [J].

WHITE, WN ;

NORCROSS, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (15) :3265-&

[35] THE STEREOCHEMISTRY OF THE ARYL PHOSPHATE/ARYL PHOSPHONATE REARRANGEMENT IN 1,3,2-OXAZAPHOSPHOLIDINE 2-OXIDES [J].

WELCH, SC ;

LEVINE, JA ;

BERNAL, I ;

CETRULLO, J .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) :5991-5995

[36] NUCLEOPHILIC DISPLACEMENTS OF N-ARYL AND HETEROARYL GROUPS .3. PYRYLIUM-MEDIATED SYNTHESIS OF UNSYMMETRICAL DIARYLAMINES FROM ANILINES [J].

KATRITZKY, AR ;

COZENS, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (11) :2611-2615

[37] SYNTHESIS AND REARRANGEMENT OF CONFORMATIONALLY HOMOGENEOUS THIANE-1-N-ARYLIMIDES AND 1,3-DITHIANE-1-N-ARYLIMIDES [J].

CLAUS, PK ;

RIEDER, W ;

VIERHAPPER, FW .

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1975, 170 (AUG24) :112-112

[38] TRIAZENE REARRANGEMENT .3. A KINETIC STUDY OF REARRANGEMENT OF N-METHYLDIARYLTRIAZENES [J].

YAMADA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1969, 42 (12) :3565-+

[39] Gold(I)-Catalyzed Rearrangement of N-Aryl 2-Alkynylazetidines to Pyrrolo[1,2-a]indoles [J].

Kern, Nicolas ;

Hoffmann, Marie ;

Blanc, Aurelien ;

Weibel, Jean-Marc ;

Pale, Patrick .

ORGANIC LETTERS, 2013, 15 (04) :836-839

[40] Tandem Aryne-Capture/Sigmatropic Rearrangement as a Metal-Free Entry to Functionalized N-Aryl Pyrrolidines [J].

Moss, Sam G. ;

Pocock, Ian A. ;

Sweeney, Joseph B. .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (01) :101-104

← 1 2 3 4 5 →