Barium manganate in microwave-assisted oxidation reactions: synthesis of lactones by oxidative cyclization of diols

被引：35

作者：

Bagley, Mark C. ^{[1
]}

Lin, Zhifan ^{[1
]}

Phillips, David J. ^{[1
]}

Graham, Andrew E. ^{[1
]}

机构：

[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 49期

基金：

英国工程与自然科学研究理事会;

关键词：

WERNER-SYNDROME CELLS; HIGHLY EFFICIENT SYNTHESIS; SELECTIVE MONOACYLATION; SILICA-GEL; HEATING ELEMENTS; ALCOHOLS; DEHYDROGENATION; DIOXIDE; DESYMMETRIZATION; ELECTROOXIDATION;

D O I：

10.1016/j.tetlet.2009.09.117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Microwave irradiation of a range of diols at 150 degrees C in acetonitrile in the presence of three equivalents of barium manganate facilitates a novel tandem oxidation/heterocyclocondensation to give the corresponding lactone, including both small and medium ring lactones, in only one hour and in high yield without the need for chromatographic purification. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6823 / 6825

页数：3

共 54 条

[41] Desymmetrization of diols by a tandem oxidation/Wittig olefination reaction [J].

Phillips, David J. ;

Pillinger, Kathryn S. ;

Li, Wei ;

Taylor, Angela E. ;

Graham, Andrew E. .

CHEMICAL COMMUNICATIONS, 2006, (21) :2280-2282

[42] Investigating the existence of nonthermal/specific microwave effects using silicon carbide heating elements as power modulators [J].

Razzaq, Tahseen ;

Kremsner, Jennifer M. ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16) :6321-6329

[43] CATALYTIC OXIDATIVE COUPLING OF DIOLS BY RU3(CO)12 [J].

SHVO, Y ;

BLUM, Y ;

RESHEF, D ;

MENZIN, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 226 (01) :C21-C24

[44] Sequential and tandem oxidation/acetalization procedures for the direct generation of acetals from alcohols [J].

Smith, Brendan M. ;

Graham, Andrew E. .

TETRAHEDRON LETTERS, 2007, 48 (28) :4891-4894

[45] Mild and chemoselective synthesis of lactones from diols using a novel metal-ligand bifunctional catalyst [J].

Suzuki, T ;

Morita, K ;

Tsuchida, M ;

Hiroi, K .

ORGANIC LETTERS, 2002, 4 (14) :2361-2363

[46] Pseudo-C3-symmetric tertiary alcohol building block via group-selective hydroalumination:: A synthesis of (-)-malyngolide [J].

Suzuki, T ;

Ohmori, K ;

Suzuki, K .

ORGANIC LETTERS, 2001, 3 (11) :1741-1744

[47] OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS BY THE CATALYSIS OF PALLADIUM [J].

TAMARU, Y ;

YAMADA, Y ;

INOUE, K ;

YAMAMOTO, Y ;

YOSHIDA, Z .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) :1286-1292

[48] An aqueous silica gel disperse electrolysis system.: N-Oxyl-mediated electrooxidation of alcohols [J].

Tanaka, H ;

Kawakami, Y ;

Goto, K ;

Kuroboshi, M .

TETRAHEDRON LETTERS, 2001, 42 (03) :445-448

[49] Tandem oxidation processes using manganese dioxide: Discovery, applications, and current studies [J].

Taylor, RJK ;

Reid, M ;

Foot, J ;

Raw, SA .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (11) :851-869

[50] Rapid ring-opening reactions of epoxides using microwave irradiation [J].

Torborg, Christian ;

Hughes, David D. ;

Buckle, Richard ;

Robinson, Mathew W. C. ;

Bagley, Mark C. ;

Graham, Andrew E. .

SYNTHETIC COMMUNICATIONS, 2008, 38 (02) :205-211

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