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SnCl4-mediated reaction of ozonides with allyltrimethylsilane: formation of 1,2-dioxolanes

✍ Scribed by Patrick H. Dussault; Xuejun Liu

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
196 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

SnC14-mediated reaction of ozonides (1,2,4-trioxolanes) with aUyltrimethylsilane furnishes trimethylsilylmethyl-l,2-dioxolanes via metalated carbonyl oxides. The carbonyl oxides can arise through initial ionization of either the ether or peroxide oxygens.

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Dedicated to Professor Dieter Seebach on the occasion of his 60th birthday (26. VI.97) 1,4-Diphenyl-2,3-dioxabicyclo[2.2.l]hept-5-ene (2), on treatment with a catalytic amount of trimethylsilyl trifluoromethanesulfonate (Me,SiOTf) in CH,CI, at -78", reacts with excess (-)-menthone (10) to give (1 S,