18357-78-3Relevant 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.
An efficient, one-pot synthesis of S-alkyl thiocarbamates from the corresponding thiols using the Mitsunobu reagent
Chaturvedi, Devdutt,Mishra, Nisha,Mishra, Virendra
, p. 355 - 357 (2008/09/21)
A novel Mitsunobu-based protocol has been developed for the synthesis of variety of S-alkyl thiocarbamates from the corresponding thiols and amines using gaseous carbon dioxide, in good to excellent yields. This protocol is mild and efficient compared to other reported methods. Georg Thieme Verlag Stuttgart.
Practical synthesis of S-alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfur
Mizuno, Takumi,Iwai, Toshiyuki,Ito, Takatoshi
, p. 2869 - 2873 (2007/10/03)
An industrial and economic carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamate herbicides. In the presence of potassium carbonate and solvent DMSO, S-alkyl thiocarbamates, such as thiobencarb and orbencarb (herbicides) are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1atm, 20°C).
