On the regioselectivity of the nucleophilic aromatic photosubstitution of 4-nitroanisole. A dual mechanistic pathway

Albert Cantos; Jorge Marquet; Marcial Moreno-Mañas

doi:10.1016/S0040-4039(01)80417-2

On the regioselectivity of the nucleophilic aromatic photosubstitution of 4-nitroanisole. A dual mechanistic pathway

Albert Cantos, Jorge Marquet, Marcial Moreno-Mañas

Department of Chemistry

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

13 Citations (Scopus)

Abstract

4-Nitroanisole photoreacts with n-hexylamine and ethyl glycinate giving rise to regioselective methoxy and nitro group photosubstitutions respectively. Mechanistic evidences indicate the last is produced through a SN23Ar* reaction whereas the first arises from a radical ion pair via electron transfer from the amine to a 4-nitroanisole triplet excited state. © 1989.

Original language	English
Pages (from-to)	2423-2426
Journal	Tetrahedron Letters
Volume	30
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(01)80417-2
Publication status	Published - 1 Jan 1989

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title = "On the regioselectivity of the nucleophilic aromatic photosubstitution of 4-nitroanisole. A dual mechanistic pathway",

abstract = "4-Nitroanisole photoreacts with n-hexylamine and ethyl glycinate giving rise to regioselective methoxy and nitro group photosubstitutions respectively. Mechanistic evidences indicate the last is produced through a SN23Ar* reaction whereas the first arises from a radical ion pair via electron transfer from the amine to a 4-nitroanisole triplet excited state. {\textcopyright} 1989.",

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AU - Cantos, Albert

AU - Marquet, Jorge

AU - Moreno-Mañas, Marcial

PY - 1989/1/1

Y1 - 1989/1/1

N2 - 4-Nitroanisole photoreacts with n-hexylamine and ethyl glycinate giving rise to regioselective methoxy and nitro group photosubstitutions respectively. Mechanistic evidences indicate the last is produced through a SN23Ar* reaction whereas the first arises from a radical ion pair via electron transfer from the amine to a 4-nitroanisole triplet excited state. © 1989.

AB - 4-Nitroanisole photoreacts with n-hexylamine and ethyl glycinate giving rise to regioselective methoxy and nitro group photosubstitutions respectively. Mechanistic evidences indicate the last is produced through a SN23Ar* reaction whereas the first arises from a radical ion pair via electron transfer from the amine to a 4-nitroanisole triplet excited state. © 1989.

U2 - 10.1016/S0040-4039(01)80417-2

DO - 10.1016/S0040-4039(01)80417-2

M3 - Article

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VL - 30

SP - 2423

EP - 2426

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

On the regioselectivity of the nucleophilic aromatic photosubstitution of 4-nitroanisole. A dual mechanistic pathway

Abstract

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