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1,3-Dipolar Cycloadditions to Strained Olefins

✍ Scribed by Konrad B. Becker; Martin K. Hohermuth

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
764 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The Bredt olefins bicyclo [3.3.1]non‐1‐ene (2), bicyclo [4.2.1]non‐1 (8)‐ene (3), and bicyclo [4.2.1]non‐1 (2)‐ene (4) react rapidly with 1,3‐dipoles such as diazomethane, phenyl azide, and mesitonitrile oxide to yield mixtures of two regioisomeric cycloadducts 10, 11 and 12, respectively. On the contrary, cycloaddition to the comparable monocyclic 1‐methyl‐(E)‐cyclooctene (5) is fairly regioselective. 2‐Methylnorborn‐2‐ene (6) gives one isomer with mesitonitrile oxide (as do less strained olefins), but mixtures with diazomethane and phenyl azide. ^1^H‐NMR. and ^13^C‐NMR. spectra of the cycloadducts are reported. The results are discussed in the light of frontier molecular orbital theory.

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