27846-22-6Relevant academic research and scientific papers
Kinetics and Mechanism of the Oxidation of n-Dodecanethiol and Pyridine-Substituted Ethanethiols by I2 in Acetonitrile
deLeeuw, David L.,Musker, W. Kenneth,Doi, Joyce Takahashi
, p. 4860 - 4864 (1982)
Our investigations of the iodine oxidation of divalent sulfur have been extended to include the thiol group.In acetonitrile the rates of iodine oxidation of thiols can be measured at 25.0 deg C by using stopped-flow techniques.The oxidation of the isomeri
Photochemical metal-free aerobic oxidation of thiols to disulfides
Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
supporting information, p. 546 - 551 (2021/01/28)
Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is
Thermal conversion of primary alcohols to disulfides: Via xanthate intermediates: An extension to the Chugaev elimination
He, Wei,Ding, Yong,Tu, Jianzhuo,Que, Chuqiang,Yang, Zhanhui,Xu, Jiaxi
, p. 1659 - 1666 (2018/03/21)
Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially available primary alkanols.
A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water
Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
, p. 41 - 44 (2017/09/25)
A one-pot and efficient synthesis of dialkyl dichalcogenides (S, Se) in aqueous media under catalyst-free conditions using benzylic, allylic and primary halides with elemental sulfur and selenium has been developed. Also, this procedure was extended to preparation of trisulfides and triselenides from secondary and tertiary halides in same condition. In all cases, products can be obtained in good to excellent yield in short reactions time.
AGENT FOR INTRODUCING PROTECTING GROUP FOR HYDROXY GROUP AND/OR MERCAPTO GROUP
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Paragraph 0058, (2017/11/11)
A novel agent for introducing a protecting group for a hydroxy group and/or a mercapto group that can be introduced and removed under mild conditions is provided. The agent for introducing a protecting group for a hydroxy group and/or mercapto group of a substrate compound having the hydroxy group and/or mercapto group is represented by the following formula (I), wherein A represents a ring structure having 1 to 5 rings in which two carbon atoms of an adjacent benzene ring are included, the ring structure comprises a substituted or unsubstituted five-membered ring or six-membered ring and optionally include a heterocycle; each of R1, R2, R3, and R4 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms; and X is a halogen atom or OSO2R5 (R5=an aryl group or an alkyl group).
Simple and green method for synthesis of symmetrical dialkyl disulfides and trisulfides from alkyl halides in water; PMOxT as a sulfur donor
Soleiman-Beigi, Mohammad,Mohammadi, Fariba
, p. 134 - 141 (2017/03/07)
An environmentally new, mild and efficient method has been developed for the synthesis of dialkyl disulfides and dialkyl trisulfides in aqueous conditions by a reaction between alkyl halides (and tosylate) and potassium-5-methyl-1,3,4-oxadiazole-2-thiolate (PMOxT) as a sulfur transfer reagent. The advantages of this method are that it occurs under mild reaction conditions, it is base free, it uses water as the solvent and it occurs in high yields. A variety of dialkyl disulfides and dialkyl trisulfides can be obtained in good to excellent yields up to 98%.
Dithioacetal Exchange: A New Reversible Reaction for Dynamic Combinatorial Chemistry
Orrillo, A. Gastón,Escalante, Andrea M.,Furlan, Ricardo L. E.
supporting information, p. 6746 - 6749 (2016/05/11)
Reversibility of dithioacetal bond formation is reported under acidic mild conditions. Its utility for dynamic combinatorial chemistry was explored by combining it with orthogonal disulfide exchange. In such a setup, thiols are positioned at the intersection of both chemistries, constituting a connecting node between temporally separated networks. In reverse: Reversibility of dithioacetal bond formation is reported under acidic mild conditions (see figure). Its utility for dynamic combinatorial chemistry was explored by combining it with orthogonal disulfide exchange. In such a setup, thiols are positioned at the intersection of both chemistries, constituting a connecting node between temporally separated networks.
Synthesis of Disulfanes from Organic Thiocyanates Mediated by Sodium in Silica Gel
Maurya, Chandra Kant,Mazumder, Avik,Kumar, Ajeet,Gupta, Pradeep Kumar
, p. 409 - 411 (2016/02/09)
We report an efficient procedure for the synthesis of symmetrical disulfanes from organic thiocyanates in the presence of sodium in silica gel at room temperature. By avoiding the use of foul-smelling thiols, the present protocol provides an attractive alternative to existing methods for the preparation of symmetrical disulfanes.
Direct synthesis of disulfides from alkyl halides using thiourea and CCl4 in glycerol
Abbasi, Mohammad,Khalili, Dariush
, p. 1425 - 1430 (2015/06/22)
Abstract Dialkyl disulfides were obtained on the basis of the reaction of alkyl halides and thiourea in the presence of CCl4 and Et3N. This procedure enables the odorless and one-pot synthesis of disulfides by employing cheap, easy-to-handle and readily available reagents and substrates in wet glycerol.
Graphene Oxide-Assisted One-Pot and Odorless Synthesis of Symmetrical Disulfides Using Primary and Secondary Alkyl Halides (Tosylates) and Thiourea as Sulfur Source Reagent
Khalili, Dariush
, p. 1727 - 1734 (2015/12/12)
Graphene oxide is described as a heterogeneous oxidant for the synthesis of symmetrical disulfides through the in situ generation of thiols from primary and secondary alkyl halides (tosylates) and thiourea in wet acetonitrile. A variety of alkyl halides and alkyl tosylates can be converted to corresponding disulfides in good to excellent yields. This strategy is free of foul-smelling thiols.
