Model Studies of β-Scission
Ring-Opening Reactions of
Cyclohexyloxy Radicals:  Application to
Thermal Rearrangements of
Dispiro-1,2,4-trioxanes

Taylor, Benjamin J.

Model Studies of β-Scission Ring-Opening Reactions of Cyclohexyloxy Radicals: Application to Thermal Rearrangements of Dispiro-1,2,4-trioxanes

Posted on 2007-12-20 - 00:00

A DFT study of model cyclohexyloxy radicals (8a−c, 9) show that (a) the presence of an adjacent oxygen atom, and (b) α-substituents on the cyclohexyl ring, particularly methoxy, accelerate the rate of β-scission ring-opening reactions. Consistent with theoretical results, thermolysis of the methoxy-substituted dispiro-1,2,4-trioxane 10 afforded the structurally novel, 14-membered macrocyclic keto lactone 11 as the major isolable product.

CITE THIS COLLECTION

Erhardt, Stefan; Macgregor, Stuart A.; McCullough, Kevin J.; Savill, Karen; Taylor, Benjamin J. (2016). Model Studies of β-Scission Ring-Opening Reactions of Cyclohexyloxy Radicals: Application to Thermal Rearrangements of Dispiro-1,2,4-trioxanes. ACS Publications. Collection. https://doi.org/10.1021/ol702534d

https://doi.org/10.1021/ol702534d

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