4010-05-3Relevant academic research and scientific papers
Sulfonyl-Promoted Michaelis-Arbuzov-Type Reaction: An Approach to S/Se-P Bonds
Rather, Suhail A.,Bhat, Mohammad Yaqoob,Hussain, Feroze,Ahmed, Qazi Naveed
, p. 13644 - 13663 (2021/10/01)
By facilitating the chemical conversion of thiols to thiosulfonates, phosphoramidite/phosphite bearing sp3-hybridized carbon serves as an ideal coupling material to forge new connections at room temperature. In this work, a functional group-induced, additive-free, novel, S-P bond-forming approach is presented. This protocol exhibits good functional group tolerance with wide applications that include phosphorylation of cysteine derivatives, development of a one-pot approach to mixed unsymmetrical thiophosphonates, and extension of the concept to different Se-P bonds. Meticulously, our reaction also generated a S-P bond against cyclic 1,2-dithiane-1-dioxide in a byproduct-free manner. These Michaelis-Arbuzov-type reactions are easy to conduct, work efficiently in a reduced reaction time, and are applicable to gram-scale preparation as well.
New and facile synthesis of thiosulfonates from sulfinate/disulfide/I2 system
Fujiki, Kiyoko,Tanifuji, Naoki,Sasaki, Yohei,Yokoyama, Taku
, p. 343 - 348 (2007/10/03)
Thiosulfonates were prepared by the iodine oxidative sulfenylation of sulfinates with various disulfides in good yields both in the presence and absence of solvent. One of the important biological applications of sulfenylation is the reaction of cyclic disulfides.
Bicyclic Vinyl Sulfides by Ring Expansions of Spirocyclic Dithioketal Systems
Nickon, Alex,Rodriguez, Abimael D.,Shirhatti, Vilas,Ganguly, Rathindra
, p. 4218 - 4226 (2007/10/02)
Our objective was to prepare sulfur-containing bicyclo- and -alkenes for future photochemical studies.Prototypes having a seven-membered heterocyclic ring with two sulfurs were obtained by one-atom ring expansion of a spirocyclic 1,3-dithiane 1-oxide (11b).A similar sequence applied to the homologous 1,3-dithiepine 1-oxide (17) enlarged it to its corresponding eight-membered heterocycle (18).A two-atom-ring growth of a β-hydroxy-1,3-dithiane promoted by P2O5 was developed with a monocyclic model compound (23a).The product (24) is a1,5-dithiacyclooctene with one sulfur vinylic and the other allylic.When the scheme was applied to the appropriate spirocyclic 1,3-dithiane system (29a), P2O5 produced the corresponding 12/8 bicyclic alkene (31a) with a tetrasubstituted ?-bond.With POCl3/Py, the 6 -> 8 rearrangement afforded the trisubstituted olefin (30a), which separately could be isomerized to alkene 31a.The action of P2O5 on a spirocyclic β-hydroxy-1,3-dithiolane (29c) gave the desired 12/7 ring system as a binary mixture of olefins (30b, 31b), which converted entirely to the more stable tetrasubstituted isomer when treated with HCl gas.One-atom (6 -> 7) ring expansion in α-hydroxy-1,3-dithianes was tested on a monocyclic analogue (32a) and its acetate ester (32b).Hot POCl3/Py successfully enlarged the alcohol to an alkene having a 1,4-dithiepane skeleton (36).Pyrolysis of the acetate (32b) effected the same ring expansion.
