Isothiocyanates unsaturated, synthesis

Reactions of unsaturated carbanions with isothiocyanates in synthesis of heterocycles 99JHC1469. 

Guthrie and Irvine35 also developed an original synthesis of unsaturated isothiocyanates, starting from a mixture of the unsaturated azido sugars 15... 

Perfluoro-2-methyl-2-penten-3-yl isothiocyanate, which was prepared from perfluoro-2-methyl-2-pentene and KSCN in benzonitrile in high yield by direct substitution of fluorine, is a stable and versatile educt for heterocyclic synthesis. This a,p-unsaturated isothiocyanate reacted with enamines, such as 1-methylindole and 2-methyl-1-morpholino-l-propene, to yield 2-(l-methylindol-3-yl)-perfluro-4,5-dihydro-5,5-dimethyl-4-ethylidene-l,3-thiazole and its analogue in fair yield. [95H1015]... 

Synthesis of heterocyclic compounds from metallated unsaturated compounds and isothiocyanates 00KGS1443. 

In addition to the general procedure iUusIrated by Eq. (2.182), another route has been employed for the synthesis of metal alkoxides (and particularly analogous siloxides) by the reaction of metal alkoxides with esters (and silyl esters) (Section 4.3). Further, the reactions of metal alkoxides with acyl halides (or hydrogen halides) and unsaturated substrates such as CO, CO2, CS2, organic-isocyanates and isothiocyanates, chloral, etc. have been utilized for the preparation of haUde-alkoxides (Section 4.11) and interesting insertion products (Section 4.12), respectively. 

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