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- W201607435 abstract "The electronic stability of the 1, 6-methano[11]annulenium ion (II), a Hückel-type 10π -carbonium ion, suggested the interesting possibility that keto- and ketohydroxy-derivatives of (II) would have properties analogous to those of tropone and the tropolones. Employing valence isomerizations of various types as a synthetic tool, 4, 9-methano[11]-annulenone (XV) and some of its isomers as well as 2-hydroxy-4, 9-methano[11]annulenone (XXXIV) have been prepared. In accord with expectations, these compounds qualify as homologs of tropone and the tropolones, respectively. Reinforcing this parallel, the heteroannulenes 4, 9-methano-oxa[11]annulene (XLIVa) and 4, 9-methano-thia[11]annulene (XLIVb), derived from (II) by replacement of a CH-group by oxygen or sulfur, appear to correlate with the heterotropilidenes. In further extension of this concept the synthesis of the extraordinarily stable 14π -carbonium ion (LI) has been achieved recently." @default.
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- W201607435 date "1971-01-01" @default.
- W201607435 modified "2023-10-16" @default.
- W201607435 title "10π-ELECTRON ANALOGS OF TROPYLIUM ION, TROPONE AND THE TROPOLONES" @default.
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- W201607435 doi "https://doi.org/10.1016/b978-0-408-70315-4.50016-1" @default.
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