Phosphorus, Sulfur and Silicon and the Related Elements p. 1503 - 1513 (2014)
Update date:2022-08-11
Topics:
Ivanov, Ivaylo K.
Parushev, Ivaylo D.
Christov, Valerij Ch
Reaction of 4-sulfinylated or 4-sulfonylated allenecarboxylates with different electrophilic reagents such as sulfuryl chloride, bromine, benzenesulfenyl, and benzeneselenenyl chlorides takes place with 5-endo-trig cyclization or 3,2-addition reaction depending on the kind of the substituent at the sulfur atom. Treatment of 4-(benzenesulfinyl)-allenoates with electrophiles gives 5-(benzenesulfinyl)-2,5-dihydrofuran-2-ones as a result of the neighboring carboxylate group participation in the cyclization. On the other hand, (3E)-4-(methansulfonyl)alk-3-enoates were prepared by chemo-, regio-, and stereoselective electrophilic addition to the C2-C3-double bond in the allenoate moiety of 4-(methanesulfonyl)allenecarboxylates. When R1 = Me, the treatment with electrophiles gives mixtures of (3E)-4-(methanesulfonyl)alk-3-enoates and (3E)-4-(methanesulfonyl)-2-methylenealk-3-enoates with ratios of about 1.6:1 as a result of addition and elimination reactions. A possible mechanism involving cyclization, addition, and elimination reactions of the 4-sulfinylated or 4-sulfonylated allenecarboxylates is proposed.
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