Isothiocyanate
From Free net encyclopedia
Isothiocyanate is the chemical group -N=C=S, formed by substituting sulfur for oxygen in the isocyanate group. Allyl isothiocyanate is also called mustard oil.
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Reactions
Isothiocyanates act as electrophiles with the carbon atom as the electrophilic center. This is demonstrated by the reaction of the acetophenone enolate with phenyl isothiocyanate. In this one-pot synthesis Template:Ref the ultimate reaction product is a Thiazolidine. This reaction is stereoselective with the formation of the Z-isomer only as evidenced by the Nuclear Overhauser effect in the proton NMR spectrum.
Image:ThiazolidineSynthesis.gif
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References
- Template:Note Improved approaches in the synthesis of new 2-(1, 3-thiazolidin-2Z-ylidene)acetophenones M. Carmen Ortega-Alfaro, José G. López-Cortés, Hiram Rangel Sánchez, Rubén A. Toscano, Guillermo Penieres Carrillo, and Cecilio Álvarez-Toledano Arkivoc (EJ-1528C) pp 356-365 2005 Online article