%0 Journal Article %A Hoijemberg, Pablo A. %A Moss, Robert A. %A Feinblum, David V. %A Krogh-Jespersen, Karsten %D 2014 %T O‑Ylide and π‑Complex Formation in Reactions of a Carbene with Dibenzo and Monobenzo Crown Ethers %U https://acs.figshare.com/articles/journal_contribution/_i_O_i_Ylide_and_Complex_Formation_in_Reactions_of_a_Carbene_with_Dibenzo_and_Monobenzo_Crown_Ethers/2264872 %R 10.1021/jp506154s.s001 %2 https://acs.figshare.com/ndownloader/files/3900877 %K studies support %K complex %K Monobenzo Crown EthersReactions %K dibenzo crown ethers %K PNPCC %K monobenzo crown ethers %X Reactions of p-nitrophenylchlorocarbene (PNPCC) with various dibenzo crown ethers produce O-ylides and π-complexes; the reactions can be followed via the spectral signatures of the carbene and the products. The O-ylides form most rapidly, but over time they decay in favor of the more stable π-complexes. Extensive computational studies support and refine appropriate structural and mechanistic conjectures. Reactions of PNPCC with monobenzo crown ethers afford only the spectral signatures of O-ylides; monobenzo π-complexes are either not formed in significant concentrations or are spectroscopically silent. %I ACS Publications