Primary alcohol oxidation with N-iodosuccinimide

Abstract

Some time ago, we studied the reaction of secondary1 and tertiary2 alcohols with IV-iodosuccinimide (NIS). At this time, we report the oxidation of some primary alcohols with NIS. We subjected a series of eight primary alcohols to NIS oxidation with irradiation. The identity of the products obtained supports the belief8 that alkyl hypoiodites are formed when alcohols and NIS react, followed by homolytic decomposition of the intermediate hypo- 75-30-9; p-methylbenzaldehyde, 104-87-0; o-methylbenzaldehyde, 529-20-4; p-fluorobenzaldehyde, 459-57-4.

N-Halosuccinimides as Precatalysts for C-, N-, O-, and X-Nucleophilic Substitution Reactions of Alcohols under Mild Reaction Conditions

“…We found that NCS and NIS were slightly more convenient mediators for this transformation than NBS. Under the typical reaction conditions in the dark or the presence of radical scavenger, the high conversion of starting material 14 into the corresponding product 16 was established, accompanied by the formation of a small amount of dimeric ether 17 and oxidized alcohol 18 [38] (entries 5-6, Table 3). In order to support the assumption that the dimeric ether 4 might be the intermediate of this dehydrative coupling [32], few control reactions were performed (Scheme 3).…”

Use of Alcohol as Initiator for Reversible Chain Transfer Catalyzed Polymerization

“…However, the yield of 1 was moderate, i.e., 40% from the starting benzyl alcohol. A side reaction was the formation of benzaldehyde ( 2 ) via the disproportionation of RO • with I • or another RO • (path 3 in Scheme ) or the intramolecular elimination of RO–I (path 4 in Scheme ) 11. The yield of 2 was 12%.…”

N-Iodosuccinimide-Mediated Dimerization of 2-Alkynylnaphthols: A Highly Diastereoselective Construction of Bridged Polycyclic Compounds via Vinylidene ortho-Quinone Methide Intermediate

“…We commenced our investigation with 1a as the substrate and NIS as the promoter in the presence of dichloromethane. To our delight, the reaction went smoothly to give 2a as a single product in almost quantitative yield (Table , Entry 1).…”