1, 3‐Dipolar Cycloaddition of 4‐Chlorobenzonitrile Oxide with Some Dipolarophiles: Theoretical Analysis of Regioselectivity. (7th March 2013)

• Record Type: Journal Article
• Authors: Bakavoli, Mehdi; Moeinpour, Farid; Sardashti‐Birjandi, Arezoo; Davoodnia, Abolghasem
• Is Part Of: Journal of heterocyclic chemistry. Volume 50:Number 2(2013:Mar.)
• Page Start: 188
• Page End: 193
• Publication Date: 2013-03-07
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.822
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main" xml:lang="en" id="jhet822-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p id="jhet822-para-0002">Reaction of 4‐chlorobenzonitrile oxide (<xref ref-type="link" rid="jhet822-fig-0001">1</xref>) which was generated <italic>in situ</italic> with acrylo nitrile (<bold>3</bold>), vinyl acetate (<xref ref-type="link" rid="jhet822-fig-0001">1</xref>) and allyl bromide (<xref ref-type="link" rid="jhet822-fig-0001">1</xref>) as dipolarphile afforded the new cycloadducts <xref ref-type="link" rid="jhet822-fig-0001">1</xref>, <xref ref-type="link" rid="jhet822-fig-0001">1</xref>, and <xref ref-type="link" rid="jhet822-fig-0001">1</xref> compounds, respectively. Reactivity and regiochemistry of these reactions were investigated using activation energy calculations and density functional theory‐based reactivity indexes. The theoretical ¹³C NMR chemical shifts of the cycloadducts which were obtained by gauge‐invariant atomic orbital method were comparable with the observed values.</p> </abstract>