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1,8-Bis(tetramethylguanidino)naphtalene (TMGN): a new superbasic and kinetically active „proton sponge

Raab, V. ; Kipke, J. ; Gschwind, R. M. ; Sundermeyer, J.



Abstract

1,8-Bis(tetramethylguanidino)naphthalene (TMGN, 1) is a new, readily accessible, and stable proton sponge with an experimental pKBH+ value of 25.1 in MeCN, which is nearly seven orders of magnitude higher in basicity than the classical proton sponge 1,8-bis(dimethylamino)-naphthalene (DMAN). Because of the sterically less crowded character of the proton-accepting sp2-nitrogen atoms, TMGN also has ...

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