The gas-phase elimination reaction of 3-methoxycyclohexene: regiochemistry

John J. Rabasco; Steven R. Kass

doi:10.1016/S0040-4039(00)79867-4

The gas-phase elimination reaction of 3-methoxycyclohexene: regiochemistry

John J. Rabasco, Steven R. Kass

Chemistry (Twin Cities)

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12 Scopus citations

Abstract

Gas-phase elimination reactions of deuterium labeled 3-methoxycyclohexenes have been investigated. 1,4-Elimination is heavily favored over 1,2-elimination when strong bases such as hydroxide and amide are used. The 1,2-pathway becomes more competitive when weaker bases such as methoxide are employed, and the mechanism shifts from E1 cB to E2.

Original language	English (US)
Pages (from-to)	4077-4080
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)79867-4
State	Published - Aug 12 1991

Bibliographical note

Funding Information:
.Acknowl edgement: Support from the National Science Foundation (CHE-8907 198)a nd the donors of the PetroleumR esearchF oundationa rc gratefullya cknowledged.

Keywords

3-methoxycyclohexene
elimination
flowing afterglow
gas-phase
regiochemistry

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title = "The gas-phase elimination reaction of 3-methoxycyclohexene: regiochemistry",

abstract = "Gas-phase elimination reactions of deuterium labeled 3-methoxycyclohexenes have been investigated. 1,4-Elimination is heavily favored over 1,2-elimination when strong bases such as hydroxide and amide are used. The 1,2-pathway becomes more competitive when weaker bases such as methoxide are employed, and the mechanism shifts from E1 cB to E2.",

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note = "Funding Information: .Acknowl edgement: Support from the National Science Foundation (CHE-8907 198)a nd the donors of the PetroleumR esearchF oundationa rc gratefullya cknowledged.",

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T2 - regiochemistry

AU - Rabasco, John J.

AU - Kass, Steven R.

N1 - Funding Information: .Acknowl edgement: Support from the National Science Foundation (CHE-8907 198)a nd the donors of the PetroleumR esearchF oundationa rc gratefullya cknowledged.

PY - 1991/8/12

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N2 - Gas-phase elimination reactions of deuterium labeled 3-methoxycyclohexenes have been investigated. 1,4-Elimination is heavily favored over 1,2-elimination when strong bases such as hydroxide and amide are used. The 1,2-pathway becomes more competitive when weaker bases such as methoxide are employed, and the mechanism shifts from E1 cB to E2.

AB - Gas-phase elimination reactions of deuterium labeled 3-methoxycyclohexenes have been investigated. 1,4-Elimination is heavily favored over 1,2-elimination when strong bases such as hydroxide and amide are used. The 1,2-pathway becomes more competitive when weaker bases such as methoxide are employed, and the mechanism shifts from E1 cB to E2.

KW - 3-methoxycyclohexene

KW - elimination

KW - flowing afterglow

KW - gas-phase

KW - regiochemistry

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JF - Tetrahedron Letters

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ER -

The gas-phase elimination reaction of 3-methoxycyclohexene: regiochemistry

Abstract

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Keywords

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