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- W2949225753 abstract "The potentiality of the masked o-benzoquinones, i.e., 6,6-dimethoxy-2,4-cyclohexadienones 5−8, to react both as dienes and dienophiles in their intermolecular reactions has been demonstrated. The masked o-benzoquinones (MOBs) 5−8 generated in situ from 2-methoxyphenols 1−4 underwent intermolecular Diels−Alder cycloadditions with acyclic 1,3-dienes 9a−e to provide bicyclo[2.2.2]octenones 10a−f−13a−f along with cis-decalin derivatives 14a−f−17a−f with regio- and stereoselectivity, except in the case of MOB 8. The formation of cis-decalins in these Diels−Alder reactions illustrates the dienophilic character of MOBs, in addition to their general behavior as dienes. The ratio of the two cycloadducts obtained in each reaction as a result of the dual character of MOBs depends on the nature and/or position of the substituents on both the cyclohexadienone moiety and the added conjugated acyclic diene. All of the cycloadducts resulted from the diene property of MOBs in intermolecular Diels−Alder reactions smoothly underwent Cope rearrangement to furnish cis-decalins as sole products in excellent to quantitative yields." @default.
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- W2949225753 date "2004-07-07" @default.
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- W2949225753 title "Dual Behavior of Masked <i>o</i>-Benzoquinones in Intermolecular Diels−Alder Reactions with Acyclic Dienes: A Rapid Entry to Polyfunctionalized Bicyclo[2.2.2]oct-5-en-2-ones and <i>cis</i>-Decalins" @default.
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- W2949225753 doi "https://doi.org/10.1021/jo0494580" @default.
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