Barriers to the inversion of the six-memebered rings formed by bridging the 1- and 8-positions of naphthalene with a CH2–X–CH2 chain (X = O,S,Se, or Te) increase along the series, O<S<Se<Te, in marked contrast with the corresponding pentamethylene heterocycles, reflecting the importance of bond angle strain during inversion.
J. E. Anderson, F. S. Jørgensen and T. Thomsen, J. Chem. Soc., Chem. Commun., 1982, 333 DOI: 10.1039/C39820000333
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