Abstract
Phenylethynyl sulfones of the general formula RSO2C≡CPh (R = p-Tol, Ph, CH3) undergo a photochemically induced anti-stereoselective addition to the central C1–C7 bond of 1-bromotricyclo[4.1.0.02,7]heptane to form monoadducts of the bicyclo[3.1.1]heptane (norpinic) series containing a syn-sulfonyl group in position 7 and a phenylethynyl moiety on C6. Treatment of the synthesized adducts with potassium tert-butylate in THF leads to 1,3-dehydrobromination to give sulfonyl-substituted 1-(phenylethynyl)tricyclo[4.1.0.02,7]heptanes.
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