Thiiranes

Sander, M.

doi:10.1021/cr60241a004

Cited by 260 publications

(110 citation statements)

References 117 publications

(278 reference statements)

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“…1,2,5,12,13 Reaction was carried out in cosolvent of water and ethanol at low temperature, which successfully minimized the threat of toxic and volatile organic solvents to the environment. However, according to the previous works, this method suffered from a drawback of low yield of reaction and long reaction time.…”

Section: Introductionmentioning

confidence: 99%

Study on the synthesis of thiirane

Cheng

Zhang

2006

J of Applied Polymer Sci

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ABSTRACT:In this study, a thiirane resin was synthesized by the reaction of corresponding epoxy resin with KSCN. The synthetic conditions influencing the conversion of epoxy group were systematically investigated, such as the reaction temperature, reaction media, reaction time and the ratio of KSCN to epoxy group. It was found that the conversion of epoxy group increased with the increasing reaction temperature, improving the solubility of the mediate, extending reaction time, and the enhancing ratio of salt (KSCN) to epoxy group. Wherein, the reaction temperature and the ratio of the KSCN to epoxy group were more effective. For example, when the molar ratio of KSCN to epoxy group was equal to 2.0, the conversion of epoxy group got the maximum value, 0.65. In addition, the hot plate method was used to measure the gelling time of the resultant thiirane resin at different temperatures. It was found that the gelling time was reduced to 47-85% times as the corresponding epoxy resin depending on the conversion of the epoxy group, and the curing activation energy was diminished from 39 kJ/mol of epoxy resin to 17 kJ/mol.

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Section: Introductionmentioning

confidence: 99%

Study on the synthesis of thiirane

Cheng

Zhang

2006

J of Applied Polymer Sci

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“…The oxidation of 9 to 3-hydroxy-2-phenylthietane 1,l-dioxide (19) with 112-chloroperbenzoic acid in the present study gave better yields (72x vs. 3&50%) than employing previously published (14,15) procedures using H,O,-HOAc. On the other hand, the oxidation of the thiolane 10 with tn-chloroperbenzoic acid gave the corresponding I, 1-dioxide 20 in only 27% yield.…”

Section: Introductionmentioning

confidence: 40%

“…Reaction of 12 with a saturated solution of l12S in NaOEt gave 3-hydroxy-3-phenylthietane (14), a light yellow foul smelling liquid, which has previously been prepared from the reaction of phenylmagnesium bromide with 3-thietanone (7). On the other hand, treatment of the epoxide 12 with a Ba(OH2) or NaOH solution saturated with H,S required heating at 80°C to give the thietane 14.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of substituted thietanes and thiolanes from α- and β-chloroepoxides and their oxidation to 1,1-dioxides

Abbott¹,

Haya²

1978

Can. J. Chem.

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Treatment of 3-chloro-1-phenylpropylene oxide-1,2 (7) or 1-chloro-4-phenylbutylene oxide-3,4 (8) with H2S saturated ethanolic NaOEt gave 3-hydroxy-2-phenylthietane (9) and 3-hydroxy-2-phenylthiolane (10) respectively. A similar treatment of 3-chloro-2-phenylpropylene oxide-1,2 (12) at low temperatures gave 3-chloro-2-hydroxy-2-phenylpropanethiol (13); at reflux temperatures or by refluxing 13 in ethanolic NaOEt, 3-hydroxy-3-phenylthietane (14) was formed.Oxidation of 9, 10, and 14 with m-chloroperbenzoic acid or H2O2–HOAc gave the respective 1,1-dioxides 19, 20, and 25. The alcohols 19 and 20 were dehydrated to their corresponding cyclic olefins through the benzylsulfonate esters. Under the conditions of the Ritter reaction 25 dehydrated to the cyclic olefin. Treatment of 19 with mineral acid gave benzyl methyl ketone, while refluxing 19 in base gave benzyl methyl sulfone. Ethoxylation of 2-phenylthiete 1,1-dioxide (23) to the 3-ethoxy derivative 34 was achieved under basic conditions. Attempted chlorination of 9 resulted in desulfurization to 3-chloropropenylbenzene (5).

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“…Since it has been reported that the reaction of diazoalkanes and elemental selenium provided selenoketones [2,4], the intermediate diazoselenoketone 4 is expected to form by the reaction of 5 with elemental selenium. It was also reported that the reactions of diazoalkanes with elemental sulfur are synthetically useful to prepare alkenes or episulfides [5][6][7]. We report here the formation of 1 by the reaction of 5 with elemental selenium in good yield and the formation of rare classes of sulfur-and selenium-containing heterocycles.…”

Section: Introductionmentioning

confidence: 66%