Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light

Lisa Marie Mohr; Thorsten Bach

doi:10.1055/s-0036-1588524

Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light

Lisa Marie Mohr, Thorsten Bach

Lehrstuhl für Organische Chemie I

Technische Universität München

Publikation: Beitrag in Fachzeitschrift › Artikel › Begutachtung

10 Zitate (Scopus)

Abstract

The title compounds were found to undergo a [2+2] photocycloaddition with olefins at λ = 419 nm in CH ₂ Cl ₂ as the solvent. The resulting cyclobutanes were isolated in yields of 32-87% (11 examples) and showed a defined relative configuration at C1/C4 in the major diastereoisomer (nitro and aryl trans). The analysis of side products and triplet sensitization experiments support a mechanistic scenario in which a 1,4-diradical is formed as a key intermediate.

Originalsprache	Englisch
Seiten (von - bis)	2946-2950
Seitenumfang	5
Fachzeitschrift	Synlett
Jahrgang	28
Ausgabenummer	20
DOIs	https://doi.org/10.1055/s-0036-1588524
Publikationsstatus	Veröffentlicht - 18 Dez. 2017

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title = "Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light",

abstract = "The title compounds were found to undergo a [2+2] photocycloaddition with olefins at λ = 419 nm in CH 2 Cl 2 as the solvent. The resulting cyclobutanes were isolated in yields of 32-87% (11 examples) and showed a defined relative configuration at C1/C4 in the major diastereoisomer (nitro and aryl trans). The analysis of side products and triplet sensitization experiments support a mechanistic scenario in which a 1,4-diradical is formed as a key intermediate.",

keywords = "cycloaddition, cyclobutanes, diastereoselectivity, nitro compounds, photochemistry, stereoselective synthesis, umpolung, visible light",

author = "Mohr, {Lisa Marie} and Thorsten Bach",

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

year = "2017",

month = dec,

day = "18",

doi = "10.1055/s-0036-1588524",

language = "English",

volume = "28",

pages = "2946--2950",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "20",

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TY - JOUR

T1 - Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light

AU - Mohr, Lisa Marie

AU - Bach, Thorsten

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

PY - 2017/12/18

Y1 - 2017/12/18

N2 - The title compounds were found to undergo a [2+2] photocycloaddition with olefins at λ = 419 nm in CH 2 Cl 2 as the solvent. The resulting cyclobutanes were isolated in yields of 32-87% (11 examples) and showed a defined relative configuration at C1/C4 in the major diastereoisomer (nitro and aryl trans). The analysis of side products and triplet sensitization experiments support a mechanistic scenario in which a 1,4-diradical is formed as a key intermediate.

AB - The title compounds were found to undergo a [2+2] photocycloaddition with olefins at λ = 419 nm in CH 2 Cl 2 as the solvent. The resulting cyclobutanes were isolated in yields of 32-87% (11 examples) and showed a defined relative configuration at C1/C4 in the major diastereoisomer (nitro and aryl trans). The analysis of side products and triplet sensitization experiments support a mechanistic scenario in which a 1,4-diradical is formed as a key intermediate.

KW - cycloaddition

KW - cyclobutanes

KW - diastereoselectivity

KW - nitro compounds

KW - photochemistry

KW - stereoselective synthesis

KW - umpolung

KW - visible light

UR - http://www.scopus.com/inward/record.url?scp=85028854873&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1588524

DO - 10.1055/s-0036-1588524

M3 - Article

AN - SCOPUS:85028854873

SN - 0936-5214

VL - 28

SP - 2946

EP - 2950

JO - Synlett

JF - Synlett

IS - 20

ER -

Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light

Abstract

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