Tetrahedron p. 1619 - 1630 (1988)
Update date:2022-09-26
Topics: Synthesis Isocyanate Substituted thiocyanate Experimental Carbamates Carbonates
Riondel, A.
Caubere, P.
Senet, J. P.
Lecolier, S.
Reactions of alkyl 1-chloroethyl carbonates 1 and 1-chloroethyl N,N-dialkyl carbamates 2 with MSCN (M=K, NH4) in acetone or in protic solvents (MeOH, HCONH2) afforded the corresponding thio- and/or isothiocyano derivates in good yields.The origin of the N-bonded compounds is discussed and it is concluded that most of these compounds must be due to a N condensation of the thiocyanate anion.During this work, we also found a new very mild method for isomerizing in good yields alkyl 1-thiocyanoethyl carbonates and 1-thiocyanoethyl N,N-dialkyl carbamates to their corresponding isothiocyano derivates.
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Doi:10.1021/jo901393y
(2009)Doi:10.3109/14756361003671078
(2011)Doi:10.1021/ol901325s
(2009)Doi:10.3987/COM-09-11668
(2009)Doi:10.1055/s-2008-1032095
(2008)Doi:10.1055/s-1988-27612
(1988)
