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Please login to access the full content or check if you have access via Variation 3: With N-tert-Butylbenzenesulfinimidoyl Chloride

DOI: 10.1055/sos-SD-026-00003

von Angerer, S.Science of Synthesis, (20052664.

One of the newer reagents applied for the oxidation of alcohols is N-tert-butylbenzenesulfinimidoyl chloride, which is employed in stoichiometric quantities[‌164‌] or in catalytic amounts.[‌165‌,‌166‌] It can also be used together with various bases, such as zinc(II) oxide[‌167‌,‌168‌] or 1,8-diazabicyclo[5.4.0]undec-7-ene,[‌164‌] or linked to a solid support.[‌169‌,‌170‌] When the oxidizing reagent is used in catalytic amounts, it is generated in situ by chlorination of N-tert-butylbenzenesulfenamide with N-chlorosuccinimide in the presence of potassium car­bon­ate and 4-Å molecular sieves, e.g. for the formation of 4-phenylcyclohexanone (61) (Scheme 39).[‌171‌] Since primary alcohols are more smoothly oxidized than secondary ones, selective oxidation of primary hydroxy groups in the presence of secondary ones can be achieved.

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