4108-56-9Relevant academic research and scientific papers
A convenient laboratory preparation of propargylthiol and its derivatives
Castro, Jaume,Moyano, Albert,Pericàs, Miquel A.,Riera, Antoni
, p. 518 - 520 (1997)
Reduction of propargyl S-thioacetate, followed by elimination of excess hydride and acidification, constitutes a practical alternative for the preparation of propargylthiol (as a solution of easily determined concentration) or of its derivatives (by trapping the intermediate thiolate with a suitable electrophile).
3-Silaazetidine: An Unexplored yet Versatile Organosilane Species for Ring Expansion toward Silaazacycles
Dong, Xue,Gao, Lu,He, Yuanhang,Li, Linjie,Song, Zhenlei,Wang, Qiantao,Wang, Wanshu,Zhou, Song
supporting information, p. 11141 - 11151 (2021/08/03)
Small-ring silacycles are important organosilane species in main-group chemistry and have found numerous applications in organic synthesis. 3-Silaazetidine, a unique small silacycle bearing silicon and nitrogen atoms, has not been adequately explored due to the lack of a general synthetic scheme and its sensitivity to air. Here, we describe that 3-silaazetidine can be easily prepared in situ from diverse air-stable precursors (RSO2NHCH2SiR12CH2Cl). 3-Silaazetidine shows excellent functional group tolerance in a palladium-catalyzed ring expansion reaction with terminal alkynes, giving 3-silatetrahydropyridines and diverse silaazacycle derivatives, which are promising ring frameworks for the discovery of Si-containing functional molecules.
Photochemical Doyle-Kirmse Reaction: A Route to Allenes
Or?owska, Katarzyna,Rybicka-Jasińska, Katarzyna,Krajewski, Piotr,Gryko, Dorota
supporting information, p. 1018 - 1021 (2020/01/31)
This Letter describes the metal-free, blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yield. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.
A Rh-catalyzed 1,2-sulfur migration/aza-Diels-Alder cascade initiated by aza-vinyl carbenoids from sulfur-tethered N-sulfonyl-1,2,3-triazoles
Jiang, Yu,Tang, Xiang-Ying,Shi, Min
supporting information, p. 2122 - 2125 (2015/02/05)
A novel Rh(ii) catalyzed intramolecular 1,2-sulfur rearrangement/intermolecular aza-Diels-Alder cascade initiated by azavinyl carbenes has been developed, efficiently affording sulfur-containing tetrahydropyridine derivatives or α,β-unsaturated imines wit
Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived from Cyclopropenes and Sulfides
Zhang, Hang,Wang, Bo,Yi, Heng,Zhang, Yan,Wang, Jianbo
supporting information, p. 3322 - 3325 (2015/07/15)
(Chemical Equation Presented) A new type of Rh2(OAc)4-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides is reported. A series of cyclopropenes were successfully employed for [2,3]-sigmatropic rearrangement by a reaction with either allylic or propargylic sulfides. Under the optimized conditions, the reaction afforded the products in moderate to excellent yields. In these transformations, the vinyl metal carbenes generated in situ from the cyclopropenes were effectively trapped by sulfides, resulting in the formation of corresponding products upon [2,3]-sigmatropic rearrangements.
Substituted ajoenes as novel anti-cancer agents
Hunter, Roger,Kaschula, Catherine H.,Parker, Iqbal M.,Caira, Mino R.,Richards, Philip,Travis, Susan,Taute, Francois,Qwebani, Thozama
supporting information; experimental part, p. 5277 - 5279 (2009/05/07)
A new synthesis of the ajoene pharmacophore core is presented involving the regioselective radical addition of a thiyl radical to a terminal alkyne as the key step. The synthesis allows structural variation of the two end groups on sulfur, and a range of novel derivatives varying the R1 group (sulfoxide end) has been prepared and tested against CT-1 transformed fibroblast cells for anti-cancer activity. The results indicate comparable or even improved activity compared to the parent natural product ajoene isomers. This opens up the way to systematically studying the biology of the ajoene core.
