Reactivity of Seven-Membered-Ring trans -Alkenes with Electrophiles

Jillian R. Sanzone; K. A. Woerpel

doi:10.1055/s-0036-1588451

Reactivity of Seven-Membered-Ring trans -Alkenes with Electrophiles

Jillian R. Sanzone, K. A. Woerpel

Chemistry

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

Abstract

Seven-membered-ring trans -alkenes containing a silicon-oxygen bond reacted rapidly with oxygen gas and electron-deficient alkenes and alkynes to give products with high selectivity. Addition of an electron-donating substituent or incorporating additional strain increased the reactivity by over two orders of magnitude. These results indicate that release of strain is not the only driving force for reactivity.

Original language	English (US)
Pages (from-to)	2478-2482
Number of pages	5
Journal	Synlett
Volume	28
Issue number	18
DOIs	https://doi.org/10.1055/s-0036-1588451
State	Published - Nov 13 2017

Keywords

alkenes
conjugate addition
cycloheptene
silicon
strained molecules

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0036-1588451

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abstract = "Seven-membered-ring trans -alkenes containing a silicon-oxygen bond reacted rapidly with oxygen gas and electron-deficient alkenes and alkynes to give products with high selectivity. Addition of an electron-donating substituent or incorporating additional strain increased the reactivity by over two orders of magnitude. These results indicate that release of strain is not the only driving force for reactivity.",

keywords = "alkenes, conjugate addition, cycloheptene, silicon, strained molecules",

author = "Sanzone, {Jillian R.} and Woerpel, {K. A.}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart.New York.",

year = "2017",

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doi = "10.1055/s-0036-1588451",

language = "English (US)",

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AU - Sanzone, Jillian R.

AU - Woerpel, K. A.

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart.New York.

PY - 2017/11/13

Y1 - 2017/11/13

N2 - Seven-membered-ring trans -alkenes containing a silicon-oxygen bond reacted rapidly with oxygen gas and electron-deficient alkenes and alkynes to give products with high selectivity. Addition of an electron-donating substituent or incorporating additional strain increased the reactivity by over two orders of magnitude. These results indicate that release of strain is not the only driving force for reactivity.

AB - Seven-membered-ring trans -alkenes containing a silicon-oxygen bond reacted rapidly with oxygen gas and electron-deficient alkenes and alkynes to give products with high selectivity. Addition of an electron-donating substituent or incorporating additional strain increased the reactivity by over two orders of magnitude. These results indicate that release of strain is not the only driving force for reactivity.

KW - alkenes

KW - conjugate addition

KW - cycloheptene

KW - silicon

KW - strained molecules

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JO - Synlett

JF - Synlett

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ER -

Reactivity of Seven-Membered-Ring trans -Alkenes with Electrophiles

Abstract

Keywords

ASJC Scopus subject areas

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