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Regioselectivity of the Hydroboration and Epoxidation of Limonene
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Katy Caselli
Regioselectivity of the Hydroboration and Epoxidation of Limonene
Sterics is the deciding factor in hydroboration which occurs at the least hindered carbon, thus you get the primary alcohol from limonene. The hydroboration of limonene is discussed here
MCPBA selectively oxidises the more substituted alkene source here so with limonene the selectivity is the reverse of the hydroboration and the cyclohexene double bond is epoxidised.
Sterics is the deciding factor in hydroboration which occurs at the least hindered carbon, thus you get the primary alcohol from limonene. The hydroboration of limonene is discussed here
MCPBA selectively oxidises the more substituted alkene source here so with limonene the selectivity is the reverse of the hydroboration and the cyclohexene double bond is epoxidised.
Thanks for your answer. Is there a reason why sterics is the deciding factor for hydroboration but not for epoxidation? Especially as BH3 (less bulky) is used instead of BHR2 as the reagent.More
That's very helpful, thank you for sharing. I think I understand why epoxidation occurs at the more substituted electron rich bond, however I am still unsure why hydroboration does not follow the same selectivity. Isn't BH3 also acting as an electrophile, so shouldn't it also be attracted to the more electron rich bond? I get why sterics would be the deciding factor if the hydroboration reagent used was bulkier, but in this case it isn't.More
Sterics is the deciding factor in hydroboration which occurs at the least hindered carbon, thus you get the primary alcohol from limonene. The hydroboration of limonene is discussed here
MCPBA selectively oxidises the more substituted alkene source here so with limonene the selectivity is the reverse of the hydroboration and the cyclohexene double bond is epoxidised.
Sterics is the deciding factor in hydroboration which occurs at the least hindered carbon, thus you get the primary alcohol from limonene. The hydroboration of limonene is discussed here
MCPBA selectively oxidises the more substituted alkene source here so with limonene the selectivity is the reverse of the hydroboration and the cyclohexene double bond is epoxidised.
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