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Topic: help with Simmons Smith reaction  (Read 1663 times)

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Offline cmoney451

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help with Simmons Smith reaction
« on: April 10, 2014, 10:22:46 PM »
Has anybody here done the Simmons-Smith, Furakawa modification (cyclopropanation of an alkene using Et2Zn, CH2I2, and TFA)?

This reaction is only working sporadically for me. I have been recovering starting material with just a bit of product. How big of an issue is oxygen in this reaction? Should I not see smoke when transferring diethylzinc to the round bottom? Is it OK to see a white precipitate when adding the CH2I2 to the diethylzinc, or should it just look cloudy?

BTW I do not have access to a glovebox or argon...

Any advice with this reaction would be greatly appreciated!!!!

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