Thiocyanogen reactions with alkenes

The reaction of thiocyanogen with alkenes in the presence of a radical inhibitor in the dark has been found to give a-isothiocyanato-/3-thiocyanates as well as the normal a/3-dithiocyanates. The orientation of the reaction and products formed... 

The problem stipulates that a bridged sulfonium ion is an intermediate. Therefore, use the tt electrons of the double bond to attack one of the sulfur atoms of thiocyanogen and cleave the S—S bond in a manner analogous to cleavage of a Br—Br bond in the reaction of bromine with an alkene. 

A series of papers detailing a continuation of the study of the synthesis and reactions of uic-iodothiocyanates and -iodoisothiocyanates has been published.Similarly, the treatment of alkenes with thiocyanogen bromide [from equimolar quantitites of bromine and thallium(i) thiocyanate] gives moder-ate-to-high yields of uic-bromothiocyanates. " Unlike the analogous vic-iodothiocyanates, the bromo-compounds are not readily isomerized to the corresponding isothiocyanates. 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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