Heteroatom Chemistry p. 193 - 198 (2004)
Update date:2022-08-16
Topics:
Hao, Wei
Fujii, Takayoshi
Dong, Tiaoling
Wakai, Youko
Yoshimura, Toshiaki
Alkoxy-λ6-sulfanenitriles were found to be versatile alkylating reagents toward various nucleophiles bearing at least one proton such as methanol, phenol, thiophenols, carboxylic acids, ptoluenesulfonic acid, hydrochloric acid, and primary and secondary amines. Reactivity of the alkoxy group of the λ6-sulfanenitriles showed an opposite trend to the usual SN2 character, i.e. Me (la), Pr (1b), and Bu (1d) ? i-Pr (1c). In the presence of p-TsOH, alkyl tosylates were predominantly formed instead of the alkylation products of nucleophiles. In addition, even a sterically hindered substrate, neopentyloxy-λ6-sulfanenitrile, was found to undergo an SN2 reaction toward thiophenol without any rearrangement product to give neopentyl phenyl sulfide in good yield.
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