Abstract
The thermal and Lewis acid catalyzed reactions of butadiene and acrolein have been analyzed theoretically. It is found that one of the two new CC bonds (C1C6) is formed mainly through charge transfer from butadiene to acrolein, whereas the other one (C2C3) is mainly formed through charge transfer from acrolein to butadiene. Owing to the electrophilicity of the dienophile, the HOMOLUMO monotransference from butadiene to acrolein becomes predominant over that from acrolein to butadiene. As a consequence, transition structures present asynchronicity and a diminution of the activation energy is produced. These effects are more accentuated for the s-cis transition structures given the greater electrophilicity of the s-cis conformation of acrolein. The endo preference is characterized by the lesser weight of the costlier transference from the HOMO of butadiene to the NLUMO of acrolein which leads directly to no new bonding. The catalytic action of BH 3 reinforces all these effects.
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