Metal-mediated reductive hydrodehalogenation of organic halides.

The tremendous potential of cyclopropenes and methylene-cyclopropanes as multifunctional reagents in organic syntheses has only been recognized in the last decade. The use of transition metal catalysts allows an effective control of their transformations enabling highly selecitive syntheses ranging from three- to sevenmembered carbocycles. The activities in this field are summarized in this review for the first time with an emphasis on the preparative aspects of this work.

Cyclopropenes and methylenecylopropanes as multifunctional reagents in transition metal catalyzed reactions

Thermal rearrangements of vinylcyclopropanes to cyclopentenes.

Syntheses of gem-dihalocyclopropanes and their use in organic synthesis

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Structure/Chiroptics Relationships of Planar Chiral and Helical Molecules

Interconversion of [6]paracyclophane and 1,4-hexamethylene(Dewar benzene)

Studies on the formation of [5]metacyclophane

The investigation of the chemical behavior of the substituted [5] metacyclophanes revealed a rather unusual reactivity pattern. Compared to normal, planar aromatic analogues, the cyclophanes showed two remarkable trends: (1) for typical aromatic reactions (acid-catalyzed or photochemical rearrangement, reductions, Diels-Alder reactions), a strong rate enhancement was observed; (2) toward organolithium reagents, abnormal reaction pathways are followed, such as nucleophilic substitution, SET, and other radical processes. In view of the overwhelming evidence in favor of essentially undiminished aromatic delocalization, this unusual behavior must be ascribed to the special geometry of these small cyclophanes and, in particular, to the dramatic decrease of strain occurring in the initial steps of all of these reactions

W. H. De Wolf

Papers

Interconversion of [6]paracyclophane and 1,4-hexamethylene(Dewar benzene)

Studies on the formation of [5]metacyclophane

Reactivity of 8,11-dihalo[5]metacyclophanes

7,8-dimethoxycarbonyl-10,11-dimethyl[5]paracyclophane

8,11-dichloro[5]metacyclophane