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Organic Chemistry: How to form the product?

I've been trying to figure out how to make spiro(2.5)octane from methylenecyclohexane. I know that the pi bond of the methylenecyclohexane would be used to create the propane ring on spiro(2.5)octane but I'm lost as to what reaction(s) would be needed to make the product. Any help on this would be welcome. Thanks
! Screenshot_2020-12-06 methylenecyclohexane - Google Search.png

Screenshot_2020-12-06 methylenecyclohexane - Google Search.png

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Screenshot_2020-12-06 spiro(2 5) octane reaction - Google Search.png

Reply 1

Shad0w0fIntent

Hiya bud,

For this reaction, you'd be looking at the Simmons-Smith cyclopropanation.

Here's the wiki link:
https://en.wikipedia.org/wiki/Simmons%E2%80%93Smith_reaction

Reply 2

annalgam

Original post by Shad0w0fIntent

Hiya bud,

For this reaction, you'd be looking at the Simmons-Smith cyclopropanation.

Here's the wiki link:
https://en.wikipedia.org/wiki/Simmons%E2%80%93Smith_reaction

Thanks for pointing me in the right direction!