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
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
收藏
页码:11702 / 11709
页数:8
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