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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Hydrogen-bonded assemblages in 2,6-bis(hydroxymethyl)-4-R-phenol, with R = methyl, methoxy, phenoxy and
Bernardo Masci1, Pierre Thuéry
1Dipartimento di Chimica, Università 'La Sapienza', Box 34, Roma 62, Ple Aldo Moro 5, 00185 Roma, Italy.
Abstract:
Four derivatives of 2,6-bis(hydroxymethyl)phenol, with various para substituents, have been investigated; these are 2,6-bis(hydroxymethyl)-4-methylphenol, C(9)H(12)O(3), (I), 2,6-bis(hydroxymethyl)-4-methoxyphenol, C(9)H(12)O(4), (II), 2,6-bis(hydroxymethyl)-4-phenoxyphenol, C(14)H(14)O(4), (III), and 2,6-bis(hydroxymethyl)-4-[1-(4-methoxyphenyl)-1-methylethyl]phenol, C(18)H(22)O(4), (IV). All four structures display hydrogen-bonding networks resulting in sheets, with possible weak inter-sheet pi-pi interactions in one case. In all the structures but one, the molecules form centrosymmetric dimeric subunits held together by two hydrogen bonds between the hydroxymethyl groups and, in two cases, by probable pi-pi interactions.
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