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Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
N,N'-Dineopentyl-naphthalene-1,8-diamine
Ilia A Guzei1, Lara C Spencer, Nicholas J Hill
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA.
Abstract:
In the title compound, C(20)H(30)N(2), all bond distances and angles fall within the usual ranges but the C(ipso)-N distances [1.391 (5) and 1.398 (4) Å] are slightly shorter than the corresponding typical average distance of 1.42 (3) Å. The N atoms may be described as pyramidal sp(3)-hybridized with an N-H⋯H-N separation of 2.07 (2) Å. This is necessitated because the two C(bridgehead)-C(ipso)-N-C torsion angles [170.6 (4) and 172.6 (3)°] would require the amine H atoms to be in prohibitively close proximity if the N atoms were assumed to be sp(2)-hybridized.
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