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Updated: Jun 5, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
Published on: February 27, 2017
Norbornane-exo-cis-2,3-diyl 1',2'-phenyl-ene orthocarbonate
1Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13, 81377 München, Germany.
The Title Compound (Systematic Name:
4,7-methano-2,2'-spirobi-[1,3-benzodioxole]), C(14)H(14)O(4), is an asymmetric spiro ester of orthocarbonic acid and two diols, viz. the aromatic benzene-1,2-diol and the aliphatic vicinal norbornane-exo-cis-2,3-diol. The orthocarbonate mol-ecule is close to having non-crystallographic C(s) symmetry. The five-membered ring stemming from the aliphatic diol has an envelope conformation. C-O bonds including the spiro-C atom span an approximately 0.07 Å range, but are within 0.02 Å of the respective distances in a density functional theory calculation, i.e. the distance difference is not caused by packing forces. Accordingly, the crystal packing is characterized by weak C-H⋯O and C-H⋯π inter-actions.
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