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Nickel(0)‐katalysierte Dimerisierung von 1,2,3‐Cycloheptatrien: Cyclobuta[1,2:3,4]dicycloheptatetraen, ein [4]Radialen‐Derivat
Author(s) -
Hashmi Stephen,
Polborn Kurt,
Szeimies Günter
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891221230
Subject(s) - chemistry , cycloheptatriene , derivative (finance) , nickel , dimethylformamide , medicinal chemistry , yield (engineering) , photochemistry , organic chemistry , materials science , solvent , financial economics , economics , metallurgy
Nickel(O)‐Catalyzed Dimerization of 1,2,3‐Cycloheptatriene: cyclobuta[1,2:3,4]dicyclopheptatetraene, a [4]Radialene Derivative Reaction of (7‐bromotricyclo[4.1.0.0 2,7 ]hept‐1‐yl)trimethylsilane ( 4 ) with cesium fluoride in dimethylformamide at room temperature in the presence of (Ph 3 P) 4 Ni afforded a 32% yield of the [4]radialene derivative 3 . The formation of 3 is interpreted as a Ni(0)‐catalyzed dimerization of the elusive 1,2,3‐cycloheptatriene ( 2 ), which is generated by thermal rearrangement of the highly strained tricyclo[4.1.0.0 2,7 ]hept‐1(7)‐ene ( 1 ). The X‐ray structure of 3 shows an essentially planar [4]radialene subunit.