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. Author manuscript; available in PMC: 2020 Oct 22.
Published in final edited form as: J Am Chem Soc. 2019 Aug 19;141(34):13619–13624. doi: 10.1021/jacs.9b06328

Scheme 1. Synthesis of Norbornadiene Polymer Building Blocksa.

Scheme 1.

Conditions: (i) Neat, pressure vessel, 200 °C, 5 h, 50%. (ii) DIBAL, THF, 0 °C, 30 min, 71%. (iii) CDTPA, EDC·HCl, DMAP, DCM, rt, 16 h, 92%. (iv) α-Bromoisobutryl bromide, pyridine, THF, 0 °C, 2 h, 72%. (v) 2,2-Bis(tert-butyldimethylsiloxymethyl)propionic acid, EDC·HCl, DMAP, DCM, rt, 2 days, 86%. (vi) TBAF, THF, rt, 2 h, 73%.