6302-94-9Relevant articles and documents
Mono- and di-alkyl-[1,3,5]-dithiazinanes and their N-borane adducts revisited. Structural and theoretical study
Flores-Parra, Angelina,Guadarrama-Pérez, Carlos,Ruiz, Juan Carlos Gálvez,Sánchez Ruiz, Sonia A.,Suarez-Moreno, Galdina V.,Contreras, Rosalinda
, p. 149 - 159 (2013/10/22)
Structural analyses of a series of 5-alkyl-[1,3,5]-dithiazinanes [R = Me (1), iPr (2), tBu (3)], their N-BH3 adducts (1BH3-3BH3) and their 2-alkyl (R0) derivatives are reported: R = Me, R0 = Me (7); R = Me, R0 iPr (8); R = iPr, R0 =Me (10); R = tBu, R0 =Me (11); and R = Me, R0 = nBu (12). The reaction of 2-lithium-5-methyl-[1,3,5]-dithiazinane (4) with I2 affords the bis-(5-methyl-[1,3,5]-dithiazinan-2-yl) (13). Isostructural compounds: [2,5,5]-trimethyl-[1,3,5]-dithiazinan-5-ium iodide (14), 5-borane-2,5-dimethyl- [1,3,5]-dithiazinane (15) and 2,5,5-trimethyl-[1,3,5,6]-dithiazaborata (16) are compared. Structures of 7, 8 and 10-13 were determined by 11B, 13C and 1H NMR and the X-ray diffraction analyses of 2, 1BH3, 13 and 14 are reported. Optimization of two chair conformers of heterocycles 1-3, 1BH3-3BH3, 7, 9 (R = Me, R0 = tBu), 13-16 were performed by HF/6-31++G and B3LYP/6-31G(d,p) methods and their minimum energy is compared. 2-Alkyl substituents or N-BH3 anchor the [1,3,5]-dithiazinane ring conformation allowing the analyses of steric and electronic interactions as well as the lone pairs effect in these molecules.
Thiomethylation of amino alcohols using formaldehyde and hydrogen sulfide
Akhmetova,Nadyrgulova,Tyumkina,Starikova,Antipin,Kunakova,Dzhemilev
, p. 918 - 925 (2008/03/11)
Three-component condensations of formaldehyde with hydrogen sulfide and hydroxylamine or amino alcohols at a ratio of 3:2:1 give 47-73% of N-hydroxy(or hydroxyalkyl)-1,3,5-dithiazinanes. The reactions of CH2O with H 2S and hydroxylamine or α-amino alcohols at a ratio of 4:3:1 involve both amino and hydroxy groups, leading to the corresponding dithiazinanes. 4-Aminobutan-1-ol reacts with CH2O and H2S under analogous conditions only at the amino group to form 4-(1,3,5-dithiazinan- 5-yl)butan-1-ol.
New 1,3,5-heterocyclohexanes: Dioxazines, oxadiazines, thiadiazines, oxathiazines and triazines and their amination, transamination and disproportionation reactions
Flores-Parra, Angelina,Sanchez-Ruiz, Sonia A.
, p. 2079 - 2092 (2007/10/03)
New 1,3,5-heterocyclohexanes: 5-alkyl-1,3,5-dioxazines (R= iPr, tBu and [R]-α-methylbenzyl), 3,5-di([R]-α-methylbenzyl)-1,3,5-oxadiazine, 3,5- di([R]-α-methylbenzyl)-1,3,5-thiadiazine, 5-isopropyl-1,3,5-oxathiazine, 1- isopropyl-3,5-dimethyl-1,3,5-triazine, 1-tert-butyl-3,5-dimethyl-1,3,5- triazine are reported. Amination and transamination reactions of 1,3,5- heterocyclohexanes were investigated. Equilibria between different heterocycles were found. 13C NMR studies allowed to observe new 1,3,5- heterocycles: 1,3,5-triazines bearing two different alkyl substituents, 3,5- ditert-butyl-1,3,5-thiadiazine, 3-tert-butyl-5-isopropyl-1,3,5-oxadiazine. 1,3,5-heterocyclohexanes present a ring fluxional behavior, the ring inversion energy was calculated for dioxazines, oxadiazine, thiadiazines and triazines.