6258-60-2Relevant articles and documents
Benzylic Thio and Seleno Newman-Kwart Rearrangements
Eriksen, Kristina,Ulfkj?r, Anne,S?lling, Theis I.,Pittelkow, Michael
, p. 10786 - 10797 (2018/09/06)
The thermally induced OBn → SBn and OBn → SeBn migration reactions facilitate the rearrangement of O-benzyl thio- and selenocarbamates [BnOC(=X)NMe2] (X = S or Se) into their corresponding S-benzyl thio- and Se-benzyl selenocarbamates [BnXC(=O)NMe2] (X = S or Se). A series of substituted O-benzyl thio- and selenocarbamates were synthesized and rearranged in good yields of 33-88%. The reaction rates are higher for substrates with electron-donating groups in the 2 or 4 position of the aromatic ring, but the rearrangement also proceeds with electron-withdrawing substituents. The rearrangement follows first-order reaction kinetics and proceeds via a tight ion pair intermediate consisting of the benzylic carbocation and the thio- or selenocarbamate moiety. Computational studies support these findings.
Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols
Maurya, Chandra Kant,Gupta, Pradeep Kumar
, p. 1649 - 1651 (2017/08/11)
In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P 2 S 5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.
A metal-free and recyclable synthesis of benzothiazoles using thiourea as a sulfur surrogate
Yin, Yan,Zhou, Hong,Liu, Xichen,Chen, Haiying,Wu, Fanhong,Zhang, Heng,Tao, Ruiheng,Cheng, Fengkai,Feng, Yangbo
, p. 1709 - 1712 (2015/03/14)
Using odorless thiourea as the S source, benzothiazoles and asymmetric disulfides could be obtained from thioformanilides through the tandem cyclization/nucleophilic addition/hydrolysis/nucleophilic substitution reaction. Furthermore, the obtained asymmetric disulfides could readily transfer to benzothiazoles after nitro-reduction and amide formation reaction. This metal-free and recyclable synthetic methodology offered a time-efficient, less expensive, and environmentally friendly alternative to multifunctional benzothiazoles.
