Abstract
A reactivity difference based on the position of substituents on cyclohexa-1,3-diene was observed for the title reaction. The effect of water as solvent was more distinct for 1-methyl-4-isopropylcyclohexa-1,3-diene than for 2-methyl-5-isopropylcyclohexa-1,3-diene or non-substituted cyclohexa-1,3-diene. The effect of NaCl (salting-out) and guanidium chloride (salting-in) was also large for 1-methyl-4-isopropylcyclohexa-1,3-diene.
Highlights
The development of organic reactions in aqueous media has been remarkable [1], especially in light of the interest in “green chemistry”
The effect of micelles [4] or Lewis acids [5], including Lewis acid-surfactant combinations [6] have been studied for the aqueous Diels-Alder reaction
We have studied the substrate dependence of the aqueous DielsAlder reaction, and here report that the position of the substituents is an important factor in the aqueous Diels-Alder reaction of cyclohexadiene derivatives
Summary
The development of organic reactions in aqueous media has been remarkable [1], especially in light of the interest in “green chemistry”. When the reaction of 1 and 4 was carried out in water, the adduct was separated as a precipitate, which was collected after 2 days of stirring at room temperature to afford 5 [8] in 67% yield (Table 1; Entry 1). The dienes having alkyl substituents, 2 and 3, were treated under the same reaction conditions giving 6 [9] and 7 [10], respectively (Entries 2,3).
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