The following question was sent to me . The answer for this question was given to me as option b

questionabout carbene inscertion

I attempted it as following , recognizing the first step as a ylide reaction with a carbonyl compound. enter image description here

In order to get option B , I have to assume ylide generating a carbene and this may insert to double bond.

I have not come across phosphorous ylide as carbene generating reagent.

My question is as follows:

Will phosphorous Ylide participate in carbene generation and insertion in the presence of double bond ?

An answer in this regard would be quite help full.

  • $\begingroup$ I wasn't sure about phosphorous ylides, but cyclopropanation would be taken place with sulfur ylides. For example, the reaction of the Corey-Chaykovsky reagent with enones give corresponding cyclopropanes by undergoing a 1,4-addition that is followed by ring closure: Tetrahedron Lett. 2003, 44(18), 3629-3630 (doi.org/10.1016/S0040-4039(03)00732-9). $\endgroup$ – Mathew Mahindaratne Mar 27 at 7:34
  • $\begingroup$ For review on above reaction: doi.org/10.1021/cr960411r $\endgroup$ – Mathew Mahindaratne Mar 27 at 7:45
  • $\begingroup$ I agree. This is not a carbene reaction. I think this takes place because of the high stability of the carbanion between the rings with elimination of Ph3P $\endgroup$ – Waylander Mar 27 at 8:29

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