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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 13, Number 1
BKCSDE 13(1)
January 20, 1992 

An Explanation of the Contrasting Reactivities of meso- and d,l-D3-Trishomocubylidene-D3-trishomocubane towards Electrophiles
Oh Seuk Lee*, Eiji Osawa
The contrasting behaviour of meso-and d,l-D3-trishomocubylidene-D3-trishomocubane (1 and 2) in the electrophilic addition reaction, the former giving rearranged spiro compound (1a and 1b) and the latter giving 1,2-adduct (2a and 2b), has been explained as arising from the secondary steric effects based on computational evidence. As the degree of out-of-plane deformation of the olefinic carbon atoms increases with reaction progress, the resulting internal congestion in the region behind the double bond becomes unbearably large in meso-1. The absence of symmetry plane across the double bond of d,l-2 helps for the closing fragments to adjust themselves.
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