01392nas a2200169   4500008004100000245013700041210006900178260000800247300001400255490000700269520072500276100002501001700002201026700001801048700002601066856013001092       2025                        eng d00aAnionic 5-endo-dig cyclizations: an experimental investigation of in-plane aromaticity involving a non-enolate carbanion nucleophile0 aAnionic 5endodig cyclizations an experimental investigation of i  cNOV  a6609-66130 v123 a<p>
	Cyclitive additions of aliphatic carbanions to non-electrophilic carbon-carbon triple bonds under mild, transition-metal-free conditions are described for the first time. These results confirm theoretical models that invoke in-plane aromaticity to predict the favorability of 5-endo-dig reactions in these systems. In contrast to related Conia-ene cyclizations (5-enolexo-endo-dig), our results generally led to cyclic and allene products in near parity ratios across a broad range of substrates, suggesting that cyclization may proceed via an early ambimodal transition state. Experimental results are presented with a view to refining existing mechanistic models for this growing class of alkyne reactions.</p>
1 aNugent, Kristina, M.1 aHintze, Silas, Q.1 aMaity, Pradip1 aLepore, Salvatore, D.  uhttps://library.ncl.res.in/content/anionic-5-endo-dig-cyclizations-experimental-investigation-plane-aromaticity-involving-non