Preparation of onium salts of a reduced anthracenone crown ether macrocycle: a reactivity series involving pyridine, phosphine, thiophene, nitrile and primary amide nucleophiles | Zendy

Mariappan Kadarkaraisamy | Zendy; Caple Gerald | Zendy; Basa Prem N. | Zendy; Sykes Andrew G. | Zendy

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Preparation of onium salts of a reduced anthracenone crown ether macrocycle: a reactivity series involving pyridine, phosphine, thiophene, nitrile and primary amide nucleophiles

Author(s) -

Mariappan Kadarkaraisamy,

Caple Gerald,

Basa Prem N.,

Sykes Andrew G.

Publication year - 2012

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.2902

Subject(s) - chemistry , reactivity (psychology) , nucleophile , pyridine , nitrile , phosphonium , amide , thiophene , organic chemistry , medicinal chemistry , carbocation , medicine , alternative medicine , pathology , catalysis

Reaction of mineral acids with a cyclic macromolecule containing a secondary alcohol produces ammonium, phosphonium, thiophene, and amide adducts via a carbocation intermediate. X‐ray crystallography confirms the structures of the products, including those when two competing nucleophiles are present. A reactivity series that mirrors the nucleophilicity index, where reactivity decreases in the order thiophene > pyridine > primary amides > alkyl nitriles >> aromatic nitriles (unreactive), results. Addition of metal ions to ammonium adducts dissolved in acetonitrile produces secondary amides via the Ritter amide synthesis. Copyright © 2012 John Wiley & Sons, Ltd.

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