13153-11-2Relevant articles and documents
Oxygen-17 Nuclear Magnetic Resonance Spectroscopy of Sulfoxides and Sulfones. Alkyl Substituent Induced Chemical Shift Effects.
Dyer, John C.,Harris, David L.,Evans, Slayton A.
, p. 3660 - 3664 (1982)
Oxygen-17 NMR chemical shifts have been determined for a number of cyclic and acyclic as well as aliphatic, olefinic, and aryl sulfoxides and sulfones.The (17)O NMR chemical shifts for the acyclic, aliphatic, and aromatic sulfoxides reported here absorb in the narrow range between δ -20 and +20, while the cyclic, aliphatic sulfoxides absorb between δ -13 and +66 relative to external (but naturally abundant) H2(17)O.The sulfonyl oxygens are deshielded relative to sulfinyl oxygens, exhibiting chemical shifts for acyclic and cyclic sulfonyl oxygens between δ 120 and 183 for the sulfones reported here.Diastereotopic sulfonyl oxygens exhibit chemical shift nonequivalence.Substituent-induced chemical shift effects by a methyl or methylene group on the sulfinyl and sulfonyl oxygens are discussed.
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Tamres,Searles
, p. 2100 (1959)
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Straightforward access to 4-membered sulfurated heterocycles: Introducing a strategy for the single and double functionalization of thietane 1-oxide
Carroccia, Laura,Degennaro, Leonardo,Romanazzi, Giuseppe,Cuocci, Corrado,Pisano, Luisa,Luisi, Renzo
, p. 2180 - 2184 (2014)
A strategy for the stereoselective functionalization of thietane 1-oxide has been developed. Mono (C2 substituted) and doubly (C2, C4 disubstituted) functionalized thietanes have been obtained from the readily available thietane 1-oxide by using the corre
Reaction of singlet oxygen with thietane. A novel example of a self-catalyzed reaction which provides evidence for a thiadioxirane intermediate
Clennan, Edward L.,Dobrowolski, Piotr,Greer, Alexander
, p. 9800 - 9803 (1995)
Singlet oxygen reacts with thietane, 1, to give the sulfoxide, 1SO, and a trace of sulfone, 1SO2. A mechanism which involves a novel substrate catalyzed interconversion of a persulfoxide and thiadioxirane intermediate is proposed. The data whic
A kinetic investigation, supported by theoretical calculations, of steric and ring strain effects on the oxidation of sulfides and sulfoxides by dimethyldioxirane in acetone
Hanson, Peter,Hendrickx, Ramon A. A. J.,Lindsay Smith, John R.
supporting information; scheme or table, p. 65 - 84 (2011/01/07)
The oxidations of alkyl 4-nitrophenyl, and dialkyl, sulfides and sulfoxides by dimethyldioxirane in acetone occur by concerted mechanisms but the sulfides respond differently from the sulfoxides to variation in the alkyl group. The reactions of the sulfides are inhibited by the steric effects of alkyl groups and these predominate over their inductive effects. By contrast, the reactions of these limited sets of sulfoxides are insensitive to alkyl steric effects but there is an indication of steric acceleration when a broader set of sulfoxides is considered. This behaviour is rationalised in terms of the differences in dipolar charge and its solvation between the ground state and transition state for the two types of substrate. The oxidations of cyclic sulfides and sulfoxides also exhibit contrasting behaviour. The reactivity of the sulfides is insensitive to ring strain but is explicable in frontier orbital terms whereas that of the sulfoxides is partly dependent upon the change in ring strain between reactant and product on oxidation, a difference rationalised in terms of the relative positions of the transition states in the reaction coordinates of the two oxidations. The reactivity of 4-, 5- and 6-membered cyclic sulfoxides is also dependent on a ring-size related property of the transition state. Calculations at the B3-LYP/6-31G* level of density functional theory on both ground states and transition states, including simulation of solvation by acetone, strongly support the mechanistic conclusions reached in this and earlier work.
Synthesis of 2-alkyl(aryl)thietanes
Volynskii,Shevchenko
, p. 109 - 117 (2008/02/03)
Thietane and its 2-substituted derivatives were synthesized. A general preparation procedure for the synthesis of thietanes bearing alkyl and aryl substituents in the α-position was developed. Using this procedure, 2-substituted thietanes can be obtained from cheap and easily accessible raw materials in three steps. 2-R-Thietanes (where R = H, CH3, C 4H9, C5H11, C6H 13, C6H5) and the corresponding sulfoxides and sulfones were synthesized and examined. Intermediate and by-products of the synthesis were studied. Nauka/Interperiodica 2007.
