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Regioselectivities of Diels-Alder cycloadditions to methoxy-substituted quinones

✍ Scribed by Inga-Mai Tegmo-Larsson; Melvin D Rozeboom; K.N Houk

Book ID
104244387
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
244 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Diels-Alder cycloadducts of unsymmetrical electron-rich dienes and methoxybenzoquinones or naphthoquinones produce adducts in which the more nucleophilic diene terminus becomes bonded to the non-methoxylated carbon.

These results support the "secondary orbital", but not the "schizophrenic", model for donor substituent effects on regioselectivity.

We recently noted that the cycloadditions of electron-rich cycloaddends to electron-deficient alkenes which are unsymmetrically substituted by slkyl substituents give anomalous regioselectivities;2 the preferred products are not those predicted by frontier molecular orbital theory.

3 That is, the LUMO coefficient of the alkyl-substituted carbon is larger than that of the unsubstituted carbon.

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