Nucleophilic reactions of heterylsilanes and heterylgermanes (review)

E. Lukevits, L. Borisova, V. Gevorgyan

Research output: Contribution to journalReview article

Abstract

We generalize data on the reactivity of furyl-, dihydrofuryl-, tetrahydrofuryl-, dihydropyranyl-, and tetrahydropyranylsilanes and -germanes in reactions with nucleophilic reagents. We show that upon reaction of heterosilanes and heterogermanes with O-, N-, C-, and H-nucleophiles, sequential substitution of the heterocycles occurs at the nucleophilic group. We consider the rearrangement of (2-tetrahydrofuryl)- and (2-tetrahydropyranyl) hydrosilanes with ring expansion, and also rearrangement of linear acyloxymethyl- and halomethylhydrosilanes to the corresponding acyloxy- and halosilanes.

Original languageEnglish (US)
Pages (from-to)735-743
Number of pages9
JournalChemistry of Heterocyclic Compounds
Volume29
Issue number7
DOIs
StatePublished - Jul 1993
Externally publishedYes

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Nucleophiles
Substitution reactions

ASJC Scopus subject areas

  • Organic Chemistry

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Nucleophilic reactions of heterylsilanes and heterylgermanes (review). / Lukevits, E.; Borisova, L.; Gevorgyan, V.

In: Chemistry of Heterocyclic Compounds, Vol. 29, No. 7, 07.1993, p. 735-743.

Research output: Contribution to journalReview article

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AB - We generalize data on the reactivity of furyl-, dihydrofuryl-, tetrahydrofuryl-, dihydropyranyl-, and tetrahydropyranylsilanes and -germanes in reactions with nucleophilic reagents. We show that upon reaction of heterosilanes and heterogermanes with O-, N-, C-, and H-nucleophiles, sequential substitution of the heterocycles occurs at the nucleophilic group. We consider the rearrangement of (2-tetrahydrofuryl)- and (2-tetrahydropyranyl) hydrosilanes with ring expansion, and also rearrangement of linear acyloxymethyl- and halomethylhydrosilanes to the corresponding acyloxy- and halosilanes.

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