Improved procedure for the synthesis of enamine N-oxides

被引：12

作者：

Bernier, David ^{[1
]}

Blake, Alexander J. ^{[1
]}

Woodward, Simon ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/jo8002166

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved procedure for the preparation of enamine N-oxides involving aminolysis of epoxides, chlorination, N-oxidation, and dehydrochlorination is described. Although isolated beta-chloroamine N-oxides are prone to rearrangements when isolated, these side reactions can be slowed by the presence of stabilizing organic acids. The scope and limitations of this strategy are discussed.

引用

页码：4229 / 4232

页数：4

共 50 条

[1] DIMETHYLDIOXIRANE OXIDATION OF ENAMINES - 1ST SPECTRAL EVIDENCE FOR ENAMINE OXIDES BY STABILIZATION THROUGH N-SILYLATION [J].

ADAM, W ;

AHRWEILER, M ;

PAULINI, K ;

REISSIG, HU ;

VOERCKEL, V .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (12) :2719-2721

[2]

ALBINI A, 1993, SYNTHESIS-STUTTGART, P2263

[3] Fast synthesis of aromatic aldehydes from benzylic bromides without solvent under microwave irradiation [J].

Barbry, D ;

Champagne, P .

TETRAHEDRON LETTERS, 1996, 37 (43) :7725-7726

[4] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].

Beesley, RM ;

Ingold, CK ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106

[5]

BEHRMAN EJ, 1992, J CHEM SOC P1, V3, P305

[6] STUDIES ON THE OXIDATION OF ENAMINES WITH MOLECULAR-OXYGEN .2. OXIDATION OF 1-AMINO BUT-1-ENES [J].

BLAU, K ;

KAPST, U ;

VOERCKEL, V .

JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (04) :671-676

[7] OXIDATION OF SOME PIPERIDINO ALKENES [J].

BLAU, K ;

VOERCKEL, V .

JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (02) :285-292

[8] UNEXPECTED PRODUCTS FROM THE REACTION OF TERT-BUTOXYL RADICALS WITH ACETYLENES IN THE PRESENCE OF AN AMINOXYL RADICAL SCAVENGER [J].

BOTTLE, S ;

BUSFIELD, WK ;

JENKINS, ID ;

SKELTON, BW ;

WHITE, AH ;

RIZZARDO, E ;

SOLOMON, DH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (07) :1001-1007

[9] THE PREPARATION OF ORTHO-AMINOPHENYL SULPHATES [J].

BOYLAND, E ;

MANSON, D ;

SIMS, P .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (NOV) :3623-3628

[10] Ionic liquids as a convenient new medium for the catalytic asymmetric dihydroxylation of olefins using a recoverable and reusable osmium/ligand [J].

Branco, LC ;

Afonso, CAM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (13) :4381-4389

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