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ChemInform Abstract: Regioselective Synthesis of 1H-2-Benzoselenopyrans. Reaction of 4,4′-Dimethoxyselenobenzophenone with Acetylenes.

✍ Scribed by Kentaro Okuma; Yuji Koga; Yayoi Furunushi; Kazuki Kojima; Kosei Shioji

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

1999 organo-selenium compounds, nonmetal heterocycles organo-selenium compounds, nonmetal heterocycles S 0137

25 -161

Regioselective Synthesis of 1H-2-Benzoselenopyrans. Reaction of 4,4'-Dimethoxyselenobenzophenone with Acetylenes.

-The reaction of title compound (I) with acetylenes proceeds regioselectively through [4 + 2] type cycloaddition reaction yielding benzoselenopyrans (III) and (VI). The primary [4 + 2] cycloaddition is followed by 1,3-proton shift. Interestingly, the reaction of (I) with propiolic acid (IIb) gives the nonaromatic ketone (IVb) as major product.

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