958-80-5Relevant academic research and scientific papers
Formation of Tetrahydrothiophenes via a Thia-Paternò-Büchi-Initiated Domino Photochemical Reaction
Kassir, Ahmad F.,Guillot, Régis,Scherrmann, Marie-Christine,Boddaert, Thomas,Aitken, David J.
supporting information, p. 8522 - 8527 (2020/11/12)
We have established photochemical access to thietane or tetrahydrothiophene compounds from thiobenzophenone derivatives and acrylonitrile, wherein the product selectivity is controlled by a simple adjustment of the reagent concentration in solution. Small libraries of five-membered ring sulfur-containing compounds were prepared through a thia-Paternò-Büchi reaction, followed by a previously unknown regioselective photochemical ring enlargement reaction in a domino process or a stepwise fashion. A mechanism is proposed to rationalize this ring enlargement reaction via a carbene species provided from photoexcited thiocarbonyl compounds.
Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon
Kutsumura, Noriki,Ohshita, Ryuichiro,Horiuchi, Jumpei,Tateno, Kotaro,Yamamoto, Naoshi,Saitoh, Tsuyoshi,Nagumo, Yasuyuki,Kawai, Hidetoshi,Nagase, Hiroshi
, p. 5214 - 5219 (2017/07/28)
The synthesis of novel adamantane-like cage compounds consisting of phosphorus, sulfur, and carbon atoms was developed. We examined the reaction of a variety of acetophenone derivatives with P4S10 in refluxing benzene. A novel noradamantane-like cage compound was also synthesized, when the reaction of 2’-methoxyacetophenone with P4S10 was performed in refluxing toluene. In addition, by using the adamantane-like cage compound, 4,4’-dimethoxybenzophenone and N,N-dimethylbenzamide were successfully transformed into the corresponding thioketone (98%) and benzothioamide (89%), respectively.
Stereospecific Reactions of Donor–Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes
Augustin, André U.,Sensse, Maximilian,Jones, Peter G.,Werz, Daniel B.
supporting information, p. 14293 - 14296 (2017/10/31)
Lewis-acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield when using AlCl3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur-bridged [n.2.1] bicyclic ring systems. Conversion of selenoketones, the heavier analogues, under similar conditions resulted in the formation of various tetrahydroselenophenes.
Investigations of the Thermal Responsiveness of 1,4,2-Oxathiazoles
Hewitt, Russell J.,Ong, Michelle Jui Hsien,Lim, Yi Wee,Burkett, Brendan A.
supporting information, p. 6687 - 6700 (2015/10/29)
The first systematic study of the thermal rearrangement/fragmentation of 5,5-disubstituted 1,4,2-oxathiazoles into isothiocyanates is reported. Structure-activity relationships reveal that the choice of substituent at the 5-position of the 1,4,2-oxathiazoles is the predominant factor to influence the ease of fragmentation.
On the synthesis and biological properties of isocombretastatins: A case of ketone homologation during Wittig reaction attempts
Stocker, Vivien,Ghinet, Alina,Leman, Marie,Rigo, Benoit,Millet, Regis,Farce, Amaury,Desravines, Deborah,Dubois, Joelle,Waterlot, Christophe,Gautret, Philippe
, p. 3683 - 3696 (2013/04/11)
New isocombretastatins were synthesized by reacting the corresponding phenstatin analogs with CH3PPh3Br in presence of tBuOK. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization. In particular, monomethoxylated derivatives of phenstatin and isoCA-4 exhibit similar activities to those of parent phenstatin. Attempts of the Wittig reaction on 2- (or 4-) methoxy-4′-nitrobenzophenones in the same conditions do not lead to the expected isocombretastatins but to methyleneketones with the exclusion of triphenylphosphine. A mechanism for this new ketone homologation was proposed.
A new application of rhodanine as a green sulfur transferring agent for a clean functional group interconversion of amide to thioamide using reusable MCM-41 mesoporous silica
Ray, Suman,Bhaumik, Asim,Dutta, Arghya,Butcher, Ray J.,Mukhopadhyay, Chhanda
, p. 2164 - 2170 (2013/05/08)
A novel thionation protocol for amide compounds, with the system rhodanine/secondary amine has been discovered. Clean and efficient synthesis of a variety of thioamides can be achieved through this simple and convenient method using MCM-41 mesoporous silica as an acid catalyst. For this purpose we have synthesized MCM-41 silica and characterized by using an array of sophisticated analytical techniques like BET, HR TEM, EDX, XRD, 29Si MAS NMR and FTIR. This reaction is therefore a very neat example of a functional group interconversion.
A THIONATION PROCESS AND A THIONATING AGENT
-
Page/Page column 15, (2012/08/27)
A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N
A thionation process and a thionating agent
-
Page/Page column 10, (2012/08/14)
A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.
Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone
Bergman, Jan,Pettersson, Birgitta,Hasimbegovic, Vedran,Svensson, Per H.
experimental part, p. 1546 - 1553 (2011/06/11)
Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.
