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A new strategy for the construction of polycycles bearing a nitrogen atom on the ring fusion

✍ Scribed by Reynald Deléens; Arnaud Gautier; Serge R Piettre

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
292 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Nitroethylenes bearing either a phenylthio or a phenylselenoether group in b-position are efficient synthetic equivalents of nitroacetylene. A [4+2] cycloaddition/carbenoid-mediated elimination of PhS(e)CH 3 /[4+2] cycloaddition sequence of reactions is shown to produce formal biscycloadducts of nitroacetylene in high yields. The cycloaddition reactions are activated by high-pressure and proceed with high regioselectivities and stereoselectivities.

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