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Functionalization of a Pyridine Framework through Intramolecular Reissert-Henze Reaction of N-(Carbamoyloxy)pyridinium Salts and Unexpected Insertion of Ethereal Solvents Asahara, Haruyasu Kataoka, Asuka Hirao, Shotaro Nishiwaki, Nagatoshi This is the accepted version of the following article: European Journal of Organic Chemistry, 2015(18), 3994-3999, 2015-06, which has been published in final form at http://dx.doi.org/10.1002/ejoc.201500443. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [olabout.wiley.com/WileyCDA/Section/id-820227.html]. A new strategy for synthesis of the 2-pyridyl carbamates is reported. This strategy exploits a new intramolecular transformation of an acyloxy group from N-carbamoyloxypyridinium salts (Reissert-Henze-type reaction) as the key step. Addition of a silver salt effectively accelerates the intramolecular attack of the carbonyl oxygen at the 2-position of the pyridine ring. Additionally, a new rearrangement of the acyloxy group, combined with insertion of an ethereal solvent to give pyridine derivatives having a coordinating tether, is reported. WILEY-VCH Verlag GmbH 2015-06 eng journal article AM http://hdl.handle.net/10173/1468 https://kutarr.kochi-tech.ac.jp/records/284 10.1002/ejoc.201500443 1099-0690 European Journal of Organic Chemistry 2015 18 3994 3999 https://kutarr.kochi-tech.ac.jp/record/284/files/28-45.pdf application/pdf 744.3 kB 2019-02-13