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Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle.

ABSTRACT: A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-N,N'-diisopropylisophthalamide with m-chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This compound can be used as an efficient reagent for oxidatively assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate yields.

SUBMITTER: Yoshimura A

PROVIDER: S-EPMC6009394 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle.

Yoshimura Akira A Shea Michael T MT Makitalo Cody L CL Jarvi Melissa E ME Rohde Gregory T GT Saito Akio A Yusubov Mekhman S MS Zhdankin Viktor V VV

Beilstein journal of organic chemistry 20180508

A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-<i>N,N'-</i>diisopropylisophthalamide with <i>m</i>-chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This com ...[more]

PMID: 29977373

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