Cerium(IV) Ammonium Nitrate Mediated Addition of Thiocyanate and Azide to Styrenes: Expeditious Routes to Phenacyl Thiocyanates and Phenacyl Azides

Cis-1,4-bis(triphenylphosphonium)-2-butene Peroxodisulfate as an Efficient Reagent for the Synthesis of Phenacyl Thiocyanates and Phenacyl Azides

“…[13,2] The IR spectra were recorded on a Bomem FT-IR spectrometer. 1 H NMR and 13 C NMR spectra were taken on a 400-MHz Bruker spectrometer.…”

“…These methods, however, often require drastic reaction conditions leading to poor yields of products. Recently, some methods for the synthesis of azide and thiocyanate derivatives of a-keto compounds by using cerium(IV) ammonium nitrate, [2] iodine=MeOH, [3] Me 3 SiN 3 -CrO 3 , [4] and phenacyl bromides in hydroalcoholic media [5] were reported. Peroxodisulfate ion is an excellent and versatile oxidant, used mostly for the oxidation of compounds in aqueous solution.…”

Recent advances in CAN mediated reactions in organic synthesis

“…94 The reaction of styrene with CAN and sodium azide in methanol in oxygen atmosphere led to the formation of a-azidoketone 91 whereas argon atmosphere afforded the azidomethyl ether 92 (Scheme 17). 95 Mechanistically, the azido radical formed by the oxidation of the azide anion by CAN adds to styrene yielding the benzylic radical, which is subsequently quenched by molecular oxygen to form 91. The b-methoxy and b-nitrato products can result from the quenching of the benzylic cation by methanol and nitrate, respectively.…”

Carbon-Heteroatom Bond-Forming Reactions Mediated by Cerium(IV) Ammonium Nitrate:An Overview

“…With 4-acetoxystyrene, gem-dithiocyanates are also isolated. 43 The same combination of reagents effects the thiocyanation of indole and substituted indoles (Scheme 22) 56…”