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18.12.3.1.4.1 Variation 1: From Thiocyanates and Electrophiles

DOI: 10.1055/sos-SD-018-01132

Gilchrist, T. L.Science of Synthesis, (2005181019.

The addition of electrophilic chlorides to thiocyanates is, in principle, a method for the preparation of members of this subclass. This approach is analogous to addition reactions with cyanogen chloride and with aryl cyanates (Sections 18.12.1.1.9 and 18.12.2.1.3). However, in practice the method is not widely used. The addition of chlorine in the presence of alkenes leads to the formation of the N-β-chloroalkyl derivatives 63 in moderate yields (Scheme 27).[‌74‌] N,N-Dialkylcarbonimidium chlorides also add to the triple bond to give salts 64.[‌129‌]

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