Dilithium semibullvalenide: an unusual organolithium compound extends the scope of homoaromaticity

MJ Goldstein, TT Wenzel, G Whittaker…

Index: Goldstein, M. J.; Wenzel, T. T.; Whittaker, G.; Yates, S. F. Journal of the American Chemical Society, 1982 , vol. 104, # 9 p. 2669 - 2671

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Citation Number: 13

Abstract

I 2 3 identical conditions, dihydrobullvalene is not.'Qualitative theory provides a simple explanation. The CloHlo dianion (2) is expected to be stabilized, because it is a mode (2, 0, 0) longicyclic.'The CloHl, dianion (3) is expected to be destabilized (Le., bishomo antiaromatic), because it is an 8-a-electron pericyclic3 The value of such predictions has increasingly been questioned in recent years, 4 and particularly as it applies to anion~.~~" ...