A DFT analysis of the strain-induced regioselective[2+2]cycloaddition of benzyne possessing fused four-membered ring

L. R. Domingo; P. Pérez; R. Contreras

doi:10.2174/1570178053399958

A DFT analysis of the strain-induced regioselective[2+2]cycloaddition of benzyne possessing fused four-membered ring

L. R. Domingo, P. Pérez, R. Contreras

Exact Sciences School

Research output: Contribution to journal › Review article › peer-review

15 Citations (Scopus)

Abstract

The regioselective [2+2] cycloaddition of a substituted benzyne possessing a fused four-membered ring to a ketene acetal has been theoretically studied. This cycloaddition presents a two-step mechanism that is initiated by the nucleophilic attack to the benzyne to give a zwitterionic intermediate. The analysis performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.

Original language	English
Pages (from-to)	68-73
Number of pages	6
Journal	Letters in Organic Chemistry
Volume	2
Issue number	1
DOIs	https://doi.org/10.2174/1570178053399958
Publication status	Published - 1 Feb 2005

Keywords

[2+2] Cyloadditions
Angle strain
Benzyne
DFT calculations
Regioselectivity

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

Access to Document

10.2174/1570178053399958

Cite this

@article{4797bdf3c7764870a3e9f14e572210b8,

title = "A DFT analysis of the strain-induced regioselective[2+2]cycloaddition of benzyne possessing fused four-membered ring",

abstract = "The regioselective [2+2] cycloaddition of a substituted benzyne possessing a fused four-membered ring to a ketene acetal has been theoretically studied. This cycloaddition presents a two-step mechanism that is initiated by the nucleophilic attack to the benzyne to give a zwitterionic intermediate. The analysis performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.",

keywords = "[2+2] Cyloadditions, Angle strain, Benzyne, DFT calculations, Regioselectivity",

author = "Domingo, {L. R.} and P. P{\'e}rez and R. Contreras",

year = "2005",

month = feb,

day = "1",

doi = "10.2174/1570178053399958",

language = "English",

volume = "2",

pages = "68--73",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers B.V.",

number = "1",

}

TY - JOUR

T1 - A DFT analysis of the strain-induced regioselective[2+2]cycloaddition of benzyne possessing fused four-membered ring

AU - Domingo, L. R.

AU - Pérez, P.

AU - Contreras, R.

PY - 2005/2/1

Y1 - 2005/2/1

N2 - The regioselective [2+2] cycloaddition of a substituted benzyne possessing a fused four-membered ring to a ketene acetal has been theoretically studied. This cycloaddition presents a two-step mechanism that is initiated by the nucleophilic attack to the benzyne to give a zwitterionic intermediate. The analysis performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.

AB - The regioselective [2+2] cycloaddition of a substituted benzyne possessing a fused four-membered ring to a ketene acetal has been theoretically studied. This cycloaddition presents a two-step mechanism that is initiated by the nucleophilic attack to the benzyne to give a zwitterionic intermediate. The analysis performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.

KW - [2+2] Cyloadditions

KW - Angle strain

KW - Benzyne

KW - DFT calculations

KW - Regioselectivity

UR - http://www.scopus.com/inward/record.url?scp=24944526913&partnerID=8YFLogxK

U2 - 10.2174/1570178053399958

DO - 10.2174/1570178053399958

M3 - Review article

AN - SCOPUS:24944526913

SN - 1570-1786

VL - 2

SP - 68

EP - 73

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 1

ER -

A DFT analysis of the strain-induced regioselective[2+2]cycloaddition of benzyne possessing fused four-membered ring

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this