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Syntheses and tandem Diels‐Alder reactivities of 7,7‐diphenyl‐[2.2.1]hericene (= 7‐(diphenylmethylidene)‐2,3,5,6‐ tetramethylidenebicyclo[2.2.1]heptane) and 7‐oxa[2.2.1]hericene ( = 2,3,5,6‐tetramethylidenebicyclo[2.2.1]heptan‐7‐one)
Author(s) -
Rubello Albino,
Vogel Pierre
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710538
Subject(s) - chemistry , heptane , toluene , diels–alder reaction , reactivity (psychology) , reaction rate constant , tandem , medicinal chemistry , organic chemistry , kinetics , catalysis , medicine , physics , alternative medicine , materials science , pathology , quantum mechanics , composite material
Abstract Syntheses of 7,7‐diphenyl[2.2.1]hericene ( 4 ) and 7‐oxa[2.2.1]hericene ( 5 ) are presented. Rate constants k 1 and k 2 of the two successive Diels ‐ Alder additions of ethylenetetracarbonitrile (TCE) to 4 and to 5 have been evaluated. At 25° in toluene, the rate‐constant ratio k 1 / k 2 = 260 and 21 for 4 and 5 , respectively. These results are compared with those reported for the tandem Diels ‐ Alder reactivity of 2,3,5,6‐tetramethylidenebicyclo[2.2.1]heptane and other derivatives.