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Synfacts 2012; 8(10): 1083
DOI: 10.1055/s-0032-1317270
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Use of Acetylene Gas as Dienophile in a Diels–Alder Reaction

Contributor(s):
Timothy M. Swager
,
Silvia V. Rocha
Fort EH, Jeffreys MS, Scott LT * Boston College, Chestnut Hill, USA
Diels–Alder Cycloaddition of Acetylene Gas to a Polycyclic Aromatic Hydrocarbon Bay Region.

Chem. Commun. 2012;
48: 8102-8104
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Publication History

Publication Date:
19 September 2012 (online)

 
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Key words

Diels–Alder reaction - acetylene - polycyclic aromatic hydrocarbons

Significance

The use of acetylene gas as the ­dienophile in a cycloaddition Diels–Alder reaction to the bay region of a polyaromatic hydrocarbon is reported for the first time.


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Comment

The sequence of cycloaddition followed by hydrogen elimination–rearomatization utilizing acetylene might prove to be a useful tool in the preparation of larger polyaromatic hydrocarbons, such as uniform carbon nanotubes, from small hydrocarbon templates.


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