t-Carbinamines, RR'R″CNH₂. IV. The Addition of Isothiocyanic Acid to Olefinic Compounds¹

Synthesis of Symmetrical N,N‘-Disubstituted Thioureas and Heterocyclic Thiones from Amines and CS2 over a ZnO/Al2O3 Composite as Heterogeneous and Reusable Catalyst

“…(()-1-Phenylethyl isothiocyanate (5): yield 0.36 g (22%), pale yellow oil; bp 131-134 °C/20 mmHg (lit. 24 bp 133-134 °C/ 20 mmHg).…”

Synthesis of Sulfur-Containing Morphinane Dienes

“…Treatment of the 14P-chlorocodeine tosylate (8) with KSCN in N,N--dimethylformamide (DMF) containing 10% of water (loO°C, 6 hrs) gave rise to a 1 : 1 mixture of 6-thiocyanato-6-demethoxythebaine (14) and 7-thiocyanato-6--demethoxythebaine (11). It is supposed that the C-7 substituted compound 11 produced via the 7a-thiocyanatoneopine tosylate intermediate 10 following an S,1'+E,,2concerted mechanism, and the C-6 substituted product 14 formed from the intermediates 12 and 13 according to an SN2+SNi+E,,, mechanism (Scheme 1).…”

Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

“…The first thiocarbamides were prepared ca. 150 years ago [24,25], and their chiral derivatives have been long known [26,27], but a great interest in the latter has arisen with the development of enantioselective organocatalysis.…”