Reactions of (phenylethynyl)sulfones with tricyclo[4.1.0.02,7]heptanes

Author： Masterova Yu.Yu.   Razin V.V.   Somov N.V.  

Publisher： NRC Research Press

ISSN： 1480-3291

Source： Canadian Journal of Chemistry, Vol.91, Iss.6, 2012-12, pp. : 465-471

Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.

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Abstract

Methyl-, phenyl-, p-chlorophenyl-, and p-tolyl(phenylethynyl)sulfones under photochemical or thermal initiation add to the central bicyclobutane C1–C7 bond of 1-R(H, Me, Ph)-tricyclo[4.1.0.02,7]heptanes anti-selectively, and form norpinic adducts containing a phenylethynyl group in a geminal to substituent R position, and an endo-oriented sulfonyl group in position 7. The corresponding ketones were prepared by the hydration of the anti-adducts by the method of Kucherov. The ketone with a methylsulfonyl substituent under reflux in toluene in the presence of KOH powder and the phase-transfer catalyst (TEBA-Cl) afforded the tricyclic sulfone.

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