4-Alkenyl-1,3-dioxolan-2-ones

High-yield amination of aryl-, benzyl- and alkenyl magnesium bromides has been successful using l,3-dioxolan-2-one 0-(benzenesulfonyl)oxime 61 (Scheme 66) . 

Mercury photosensitization has been used to synthesize 1,3-dioxolane dimers by dehydrodimerization. For 1,3-dioxolane itself or analogues with substitution at C-2 or C-2 and C-4, radical formation occurs at the C-2 position, whereas when substitution is at the C-4 position radical formation occurs at the 4-position. In most cases, a small amount of product from ring opening was also reported <1996TL6853>. For 2,2-dimethyl-l,3-dioxolane, radical formation occurs at the 4-position, and one common way to achieve this is the use of dimethylzinc in air. Addition of various alkenes and related groups can then be performed, such as addition to tosyl imines <2004JOC1531>, and addition to perfluorinated alkenes and alkenyl ethers <1999JFC(94)141>. 

Substitution of allyloxy derivatives. 2-Alkenyl-l,3-dioxolan-4-ones undergo ring... 

Sn displacements. 4-Alkenyl-l,3-dioxolan-2-ones undergo ring opening in the... 

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