Synthesis of thiadiazabicyclane and bis-1,3,5-dithiazinane by cyclothiomethylation of aliphatic diamines with CH2O and H2S

被引：15

作者：

Akhmetova, Vnira R. ^{[1
]}

Vagapov, Ruslan A. ^{[3
]}

Nadyrgulova, Guzel R. ^{[1
]}

Tyumkina, Tat'yana V. ^{[1
]}

Starikova, Zoya A. ^{[2
]}

Antipin, Mikhail Yu. ^{[2
]}

Kunakova, Raikhana V. ^{[1
,3
]}

Dzhemilev, Usein M. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Petrochem & Catalysis, Ufa 450075, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organomet Cpds Inst, Moscow 119991, Russia

[3] Ufa State Acad Econ & Serv, Ufa 450077, Russia

来源：

TETRAHEDRON | 2007年 / 63卷 / 47期

关键词：

thiadiazabicyclane; bis-1,3,5-dithiazinane; cyclothiomethylation; aliphatic diamines; N; S-containing heterocycles; formaldehyde; hydrogen sulfide; X-ray crystal analysis;

D O I：

10.1016/j.tet.2007.08.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclocondensation of aliphatic diamines with CH2O and H2S (1:3:2 ratio, 0 degrees C) was carried out to give thiadiazabicyclanes and dithiadiazabicyclanes (1:6:4 ratio), which were previously difficult to synthesize. Symmetric alpha,omega,-bis-1,3,5-dithiazinanes were synthesized at 80 degrees C by this reaction. The stereochemistry of thiadiazabicyclanes was assigned by H-1 and C-13 NMR spectroscopy and by theoretical DFT calculations, and of bis-dithiazinanes by X-ray diffraction study in the solid state. (c) 2007 Published by Elsevier Ltd.

引用

页码：11702 / 11709

页数：8

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