Ring opening of 1,1-dinitrocyclopropane by addition of C, N, O and S nucleophiles

被引：34

作者：

Budynina, EM ^{[1
]}

Ivanova, OA ^{[1
]}

Averina, EB ^{[1
]}

Kuznetsova, TS ^{[1
]}

Zefirov, NS ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 05期

关键词：

nucleophilic cyclopropane ring opening; doubly activated cyclopropane; 1,1-dinitrocyclopropane; 1,1-dinitropropanes;

D O I：

10.1016/j.tetlet.2005.11.129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic ring opening of 1,1-dinitrocyclopropane was Studied with diverse C,N,O and S nucleophiles. A series of 3-X-substituted-1, 1-dinitropropanes was obtained. Weak nucleophilic tertiary amines were also active in this reaction and afforded zwitterionic compounds. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：647 / 649

页数：3

共 15 条

[1] Access to 5,5′-diaryl substituted 4,5,4′,5′-tetrahydro[3,3′]bi-isoxazolyl 2,2′-dioxides, 4,5,4′,5′-tetrahydro[3,3′]bi-isoxazolyls and [3,3′]bi-isoxazolyls via an initial ring-opening of 3,4-dinitrothiophene [J].

Bianchi, L ;

Dell'Erba, C ;

Gasparrini, F ;

Novi, M ;

Petrillo, G ;

Sancassan, F ;

Tavani, C .

ARKIVOC, 2002, :142-158

[2]

Bone W. A., 1895, J CHEM SOC, V67, P108

[3] The first synthesis of 1,1-dinitrocyclopropane [J].

Budynina, EM ;

Averina, EB ;

Ivanova, GA ;

Yashin, NV ;

Kuznetsova, TS ;

Zefirov, NS .

SYNTHESIS-STUTTGART, 2004, (16) :2609-2610

[4]

Chlenov I. E., 1969, IAN SSSR KH, V18, p[2085, 1948]

[5] HIGHLY ACTIVATED CYCLOPROPANE FOR HOMOCONJUGATE REACTIONS [J].

DANISHEFSKY, S ;

SINGH, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (11) :3239-3241

[6] ELECTROPHILIC CYCLOPROPANES IN ORGANIC-SYNTHESIS [J].

DANISHEFSKY, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (02) :66-72

[7] Magnesium iodide promoted reactions of nitrones with cyclopropanes: A synthesis of tetrahydro-1,2-oxazines [J].

Ganton, MD ;

Kerr, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8554-8557

[8] NITROCYCLOPROPANES FROM NITRODIAZOMETHANES - PREPARATION AND REACTIVITY [J].

OBANNON, PE ;

DAILEY, WP .

TETRAHEDRON, 1990, 46 (21) :7341-7358

[9] NUCLEOPHILIC RING-OPENING OF ARYL-ALPHA-NITROCYCLOPROPANECARBOXYLATES WITH STERICALLY PROTECTED BUT ELECTRONICALLY EFFECTIVE CARBONYL AND NITRO-GROUP - A NEW PRINCIPLE OF ALPHA-AMINO-ACID SYNTHESIS (2-AMINOBUTANOIC ACID A4-SYNTHON) [J].

SEEBACH, D ;

HANER, R ;

VETTIGER, T .

HELVETICA CHIMICA ACTA, 1987, 70 (06) :1507-1515

[10] Enantioselective addition of nitrones to activated cyclopropanes [J].

Sibi, MP ;

Ma, ZH ;

Jasperse, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5764-5765

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