The Ritter Reaction of Tertiary Trihalomethylcarbinols and Related Substances

Kaluszyner, Ascher; Blum, Shoshana; Bergmann, Ernst D.

doi:10.1021/jo01047a527

Cited by 10 publications

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“…An early example reported in 1963 by Kaluszyner and Bergmann was the use of a large amount of concentrated H 2 SO 4 to promote the Ritter reaction of diaryltrihalomethylcarbinols 38 and MeCN or benzonitrile to prepare the corresponding acetamide or benzamide in excellent yields (Scheme 24). 39 Generally, carbenium ions were involved as intermediates in the Ritter reaction, and substituents which can stabilize the intermediate would facilitate this reaction. Most of the established catalytic Ritter reactions were limited to alcohols with α-electron-donating groups.…”

Section: C-n Bond Formationmentioning

confidence: 99%

Catalytic functionalization of tertiary alcohols to fully substituted carbon centres

et al. 2014

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The catalytic nucleophilic substitution of tertiary alcohols using carbon or heteroatom based nucleophiles is a versatile methodology for the efficient, diverse and atom economical construction of fully substituted carbon centres, including both quaternary carbons and heteroatom substituted tetrasubstituted carbons, which only produces water as the by-product. This review summarizes the recent progress in this field, including the catalytic asymmetric studies and their application in the natural product synthesis, briefly discusses the reaction mechanism and challenges, and outlines synthetic opportunities that are still open.

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Section: C-n Bond Formationmentioning

confidence: 99%

Catalytic functionalization of tertiary alcohols to fully substituted carbon centres

et al. 2014

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“…Approximately 20% of currently marketed pharmaceuticals contain fluorine. The presence of fluorine atoms in Ritter carbenium ion precursors causes no difficulties, as shown by the standard behavior of tertiary alcohol 182 in equation 127 221. Ring opening of epoxide 183 provides high regioselectivity in forming the product 184 which is the central unit of a protease inhibitor (equation 128) 222.…”

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confidence: 99%

6.07 Ritter-Type Reactions

Bishop

2014

Comprehensive Organic Synthesis II

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TheRitter Reaction

Krimen

Cota

2011

Organic Reactions

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The formation of N‐substituted amides by the addition of nitriles to alkenes in the presence of concentrated sulfuric acid was first described by Ritter in 1948. The reaction has been extended to the addition of nitriles to a wide variety of compounds capable of forming a carbonium ion, and it constitutes the only really useful procedure for the preparation of amides of tertiary carbinamines. In its most general form, the Ritter reaction involves the nucleophilic addition of a nitrile to a carbonium ion in the presence of sulfuric acid. Attention has been given to reactions in which the carbonium ion is generated in sulfuric acid, or less commonly in sulfonic acids, phosphoric acids, or boron trifluoride. For comparison, analogous reactions, which are initiated by a nitrilium ion, formed from a nitrile and a Friedel‐Crafts catalyst, have been included in this chapter.

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The Ritter Reaction of Tertiary Trihalomethylcarbinols and Related Substances

Cited by 10 publications

References 2 publications

Catalytic functionalization of tertiary alcohols to fully substituted carbon centres

Catalytic functionalization of tertiary alcohols to fully substituted carbon centres

6.07 Ritter-Type Reactions

TheRitter Reaction

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