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Paper | Special issue | Vol 37, No. 3, 1994, pp.1623-1636
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S128
Adamantylation of N-Unsubstituted Pyrazole Derivatives: Mechanistic and Structural Studies

Pilar Cabildo, Rosa María Claramunt,* Isabelle Forfar, Concepción Foces-Foces,* Antonio L. Liamas-Saiz, and José Elguero

*Departamento de Química Orgánica y Biologiá, Faclutade de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain

Abstract

Reaction of NH-pyrazoles with 1-bromoadamantane in a high pressure stainless steel autoclave gives regioselectively 1-(1-adamanty1)-or 4-(1-adamantyl)pyrazoles depending on the temperature. A series of cross-experiments allows to establish the mechanism of this reaction. The molecular structure of the most simple derivative, 4-(1-adamantyl) pyrazole (3a), has been determined. Intermolecular N-H···N hydrogen bonds hold the four independent molecules together in a helix system parallel to the c axis. The crystal is built up of two centrosymmetricaliy related helices.