Formation and stability of the 4-methoxyphenonium ion in aqueous solution

Yutaka Tsuji; Daisuke Hara; Rui Hagimoto; John P. Richard

doi:10.1021/jo202118s

Formation and stability of the 4-methoxyphenonium ion in aqueous solution

Yutaka Tsuji
, Daisuke Hara
, Rui Hagimoto
, John P. Richard

Chemistry

University at Buffalo

National Institute of Technology, Kurume College

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

9 Scopus citations

Abstract

The reaction of 2-methoxyphenylethyl tosylate (MeO-1-Ts) is first-order in [N ₃ ^-]. A carbon-13 NMR analysis of the products of the reactions of MeO-1-[α- ¹³C]Ts shows the formation of MeO-1-[β- ¹³C]OH and MeO-1-[β- ¹³C]N ₃ from the trapping of a symmetrical 4-methoxyphenonium ion reaction intermediate 2 ⁺. An analysis of the rate and product data provides a value of k _az/k _s = 83 M ^{- 1} for partitioning of 2 ⁺ between addition of azide ion and solvent. These data set a limit for the lifetime of 2 ⁺ in aqueous solution.

Original language	English
Pages (from-to)	9568-9571
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	76
Issue number	23
DOIs	https://doi.org/10.1021/jo202118s
State	Published - Dec 2 2011

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title = "Formation and stability of the 4-methoxyphenonium ion in aqueous solution",

abstract = "The reaction of 2-methoxyphenylethyl tosylate (MeO-1-Ts) is first-order in [N 3 -]. A carbon-13 NMR analysis of the products of the reactions of MeO-1-[α- 13C]Ts shows the formation of MeO-1-[β- 13C]OH and MeO-1-[β- 13C]N 3 from the trapping of a symmetrical 4-methoxyphenonium ion reaction intermediate 2 +. An analysis of the rate and product data provides a value of k az/k s = 83 M - 1 for partitioning of 2 + between addition of azide ion and solvent. These data set a limit for the lifetime of 2 + in aqueous solution.",

author = "Yutaka Tsuji and Daisuke Hara and Rui Hagimoto and Richard, \{John P.\}",

year = "2011",

month = dec,

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doi = "10.1021/jo202118s",

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volume = "76",

pages = "9568--9571",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Formation and stability of the 4-methoxyphenonium ion in aqueous solution

AU - Tsuji, Yutaka

AU - Hara, Daisuke

AU - Hagimoto, Rui

AU - Richard, John P.

PY - 2011/12/2

Y1 - 2011/12/2

N2 - The reaction of 2-methoxyphenylethyl tosylate (MeO-1-Ts) is first-order in [N 3 -]. A carbon-13 NMR analysis of the products of the reactions of MeO-1-[α- 13C]Ts shows the formation of MeO-1-[β- 13C]OH and MeO-1-[β- 13C]N 3 from the trapping of a symmetrical 4-methoxyphenonium ion reaction intermediate 2 +. An analysis of the rate and product data provides a value of k az/k s = 83 M - 1 for partitioning of 2 + between addition of azide ion and solvent. These data set a limit for the lifetime of 2 + in aqueous solution.

AB - The reaction of 2-methoxyphenylethyl tosylate (MeO-1-Ts) is first-order in [N 3 -]. A carbon-13 NMR analysis of the products of the reactions of MeO-1-[α- 13C]Ts shows the formation of MeO-1-[β- 13C]OH and MeO-1-[β- 13C]N 3 from the trapping of a symmetrical 4-methoxyphenonium ion reaction intermediate 2 +. An analysis of the rate and product data provides a value of k az/k s = 83 M - 1 for partitioning of 2 + between addition of azide ion and solvent. These data set a limit for the lifetime of 2 + in aqueous solution.

UR - https://www.scopus.com/pages/publications/82255162508

U2 - 10.1021/jo202118s

DO - 10.1021/jo202118s

M3 - Article

C2 - 22029847

SN - 0022-3263

VL - 76

SP - 9568

EP - 9571

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Formation and stability of the 4-methoxyphenonium ion in aqueous solution

Abstract

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