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The regiochemistry of the nucleophilic addition was assigned on the basis of two factors: (1) nucleophilic addition to cyclobutenediones is known to occur with high regioselectivity at the nonvinylogous ester (or vinylogous amide) carbonyl group and (2) an extensive but yet unpublished study has demonstrated highly selective nucleophilic attack at the cyclobutenedione carbonyl group most distant from sterically encumbering substituents at the 3- or 4-position of the cyclobutenedione ring.
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The regiochemistry of the nucleophilic addition was assigned on the basis of two factors: (1) nucleophilic addition to cyclobutenediones is known to occur with high regioselectivity at the nonvinylogous ester (or vinylogous amide) carbonyl group and (2) an extensive but yet unpublished study has demonstrated highly selective nucleophilic attack at the cyclobutenedione carbonyl group most distant from sterically encumbering substituents at the 3- or 4-position of the cyclobutenedione ring.
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