%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