Facile ring-expansion substitution reactions of 1,3-dithiolanes and 1,3-dithianes initiated by electrophilic reagents to produce monohalo-, -cyano-, -azido- and -thiocyanato-1,4-dithiins and-1,4-dithiepins

被引：15

作者：

Firouzabadi, H ^{[1
]}

Iranpoor, N ^{[1
]}

Garzan, A ^{[1
]}

Shaterian, HR ^{[1
]}

Ebrahimzadeh, F ^{[1
]}

机构：

[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 02期

关键词：

ring-expansion; electrophilic substitution; 1,3-dithiolane; 1,3-dithiane; 1,4-dithiin; 1,4-dithiepin; N-halosuccinimide; N-thiocyanatosuccinimide; N-cyanosuccinimide; N-azidosuccinimide;

D O I：

10.1002/ejoc.200400502

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mild and convenient methods for the high yielding ring-expansion substitution reactions of 1,3-dithiolanes and 1,3-dithianes generated from different aryl methyl ketones using different electrophilic reagents are reported. In this study, facile preparations of monohalo-, -cyano-, -azido-, -thiocyanato-1,4-dithiins and -1,4-dithiepins are described. A general mechanism is also proposed for the reactions described in this article. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：416 / 428

页数：13

共 15 条

[1]

Aloui M, 2001, SYNLETT, P797

[2]

CAPUTO R, 1991, SYNTHESIS-STUTTGART, P223

[3] Stereoselective synthesis of fully protected (S)-1,7-dioxaspiro[5,5]undec-4-ene derivatives of sugars [J].

Caputo, R ;

Ciriello, U ;

Festa, P ;

Guaragna, A ;

Palumbo, G ;

Pedatella, S .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (14) :2617-2621

[4] A new and versatile allylic alcohol anion and acyl β-anion equivalent for three-carbon homologations [J].

Caputo, R ;

Guaragna, A ;

Palumbo, G ;

Pedatella, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9369-9371

[5] DIASTEREOSELECTIVE DESULFURIZATION OF 5,6-DIHYDRO-1,4-DITHIINS - SYNTHESIS OF MUSCALURE FROM MUSCA-DOMESTICA L [J].

CAPUTO, R ;

PALUMBO, G ;

PEDATELLA, S .

TETRAHEDRON, 1994, 50 (24) :7265-7268

[6] Reactions of silica chloride (SiO2Cl)/DMSO, a heterogeneous system for the facile regeneration of carbonyl compounds from thioacetals and ring-expansion annelation of cyclic thioacetals [J].

Firouzabadi, H ;

Iranpoor, N ;

Hazarkhani, H ;

Karimi, B .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2572-2576

[7]

Firouzabadi H, 1999, SYNLETT, P413

[8] Molybdenum pentachloride (MoCl5) promotes efficient ring-expansion and ring-expansion-chlorination of 1,3-dithiolanes and 1,3-dithianes in the presence of DMSO.: Part 3 [J].

Firouzabadi, H ;

Karimi, B .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2001, 175 :199-206

[9] RING EXPANSION REACTIONS OF 1,3-DITHIOLANS AND 1,3-DITHIANS - A NEW SYNTHESIS OF DIHYDRO-1,4-DITHIINS AND DIHYDRO-1,4-DITHIEPINS [J].

FRANCISCO, CG ;

FREIRE, R ;

HERNANDEZ, R ;

SALAZAR, JA ;

SUAREZ, E .

TETRAHEDRON LETTERS, 1984, 25 (15) :1621-1624

[10] GEM-DIFLUORINATION VS 1,3-DITHIOLANE DIHYDRO-1,4-DITHIIN REARRANGEMENT - THE ROLE OF BENZYLIC CARBONS [J].

JEKO, J ;

TIMAR, T ;

JASZBERENYI, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6748-6751

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