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Indium triflate-assisted nucleophilic aromatic substitution reactions of nitrosobezene-derived cycloadducts with alcohols.

ABSTRACT: Exclusive nucleophilic aromatic substitution of hydrogen in conjunction with cleavage of the N-O bond was observed when nitrosobenzene-derived nitroso cycloadducts were treated with indium triflate in the presence of alcohols. Aromatic alkoxylated syn-1,4 aminocycloalkenol products with good to excellent regioselectivity (16:84 to 0:100, ortho:para) were obtained.

SUBMITTER: Yang B

PROVIDER: S-EPMC2805714 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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Indium triflate-assisted nucleophilic aromatic substitution reactions of nitrosobezene-derived cycloadducts with alcohols.

Yang Baiyuan B Miller Marvin J MJ

Organic letters 20100101 2

Exclusive nucleophilic aromatic substitution of hydrogen in conjunction with cleavage of the N-O bond was observed when nitrosobenzene-derived nitroso cycloadducts were treated with indium triflate in the presence of alcohols. Aromatic alkoxylated syn-1,4 aminocycloalkenol products with good to excellent regioselectivity (16:84 to 0:100, ortho:para) were obtained. ...[more]

PMID: 20000806

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