Resonance hybrids, alkylideneallyl cations

Chapter 5 by M. Fujita and T. Okuyama examines the ringopening reactions of alkylidenecyclopropanone acetals for solvolytic generation and trapping of alkylideneallyl cations (resonance hybrids of 1-vinyl-substituted vinyl cations). In Chapter 6 by V. P. Reddy et al. stable ion and computational studies of cyclobutylmethyl cations are discussed. In Chapter 7, G. I. Borodkin and V. G. Shubin discuss and... 

Alkylideneallyl cations can be described as resonance hybrids of 1-vinyl-substituted vinyl cations and allenylmethyl cations, and thus contain two reactive sites (the sp- and sp2-hybridized carbons) for nucleophilic addition (Scheme 1) (7,2). Hybridization affects the electronic and steric character of these reaction sites. The electronic property was deduced from the l3C NMR chemical shifts of alkylideneallyl cations measured under superacidic conditions (3) and also from the charge distribution calculated (4). The charge distributions are affected by substituents on the cation the sp2 carbon is more positive than the sp carbon when two methyl groups are introduced at the sp2 carbon. 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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