Hyperconjugative effects in the stereoselective ring-opening reactions of oxetenoxides

Seiji Mori; Mitsuru Shindo

doi:10.1021/ol048499f

Hyperconjugative effects in the stereoselective ring-opening reactions of oxetenoxides

Seiji Mori, Mitsuru Shindo

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

(Chemical Equation Presented) Unexpectedly, the pattern of the stereoselectivity in the ring-opening reactions of lithium oxetenoxides is not consistent with the bulkiness of substituents, and both the bulkier tert-butyl and silyl substituents favor inward rotation. With the aid of B3LYP calculations, the hyperconjugative interaction between the breaking C ¹-O σ and its anti-periplanar Z-Me (Z = Si or C) σ* orbital is found to be responsible among the secondary orbital interactions of the substituents and the oxetene moiety.

Original language	English
Pages (from-to)	3945-3948
Number of pages	4
Journal	Organic letters
Volume	6
Issue number	22
DOIs	https://doi.org/10.1021/ol048499f
Publication status	Published - Oct 28 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol048499f

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abstract = "(Chemical Equation Presented) Unexpectedly, the pattern of the stereoselectivity in the ring-opening reactions of lithium oxetenoxides is not consistent with the bulkiness of substituents, and both the bulkier tert-butyl and silyl substituents favor inward rotation. With the aid of B3LYP calculations, the hyperconjugative interaction between the breaking C 1-O σ and its anti-periplanar Z-Me (Z = Si or C) σ* orbital is found to be responsible among the secondary orbital interactions of the substituents and the oxetene moiety.",

author = "Seiji Mori and Mitsuru Shindo",

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AU - Shindo, Mitsuru

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N2 - (Chemical Equation Presented) Unexpectedly, the pattern of the stereoselectivity in the ring-opening reactions of lithium oxetenoxides is not consistent with the bulkiness of substituents, and both the bulkier tert-butyl and silyl substituents favor inward rotation. With the aid of B3LYP calculations, the hyperconjugative interaction between the breaking C 1-O σ and its anti-periplanar Z-Me (Z = Si or C) σ* orbital is found to be responsible among the secondary orbital interactions of the substituents and the oxetene moiety.

AB - (Chemical Equation Presented) Unexpectedly, the pattern of the stereoselectivity in the ring-opening reactions of lithium oxetenoxides is not consistent with the bulkiness of substituents, and both the bulkier tert-butyl and silyl substituents favor inward rotation. With the aid of B3LYP calculations, the hyperconjugative interaction between the breaking C 1-O σ and its anti-periplanar Z-Me (Z = Si or C) σ* orbital is found to be responsible among the secondary orbital interactions of the substituents and the oxetene moiety.

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ER -

Hyperconjugative effects in the stereoselective ring-opening reactions of oxetenoxides

Abstract

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