39093-07-7Relevant academic research and scientific papers
Assignments of the Carbon Resonances in tert-Butylated 2-Naphthols by the Two-Dimensional C-Relayed H,C-COSY Technique
Kessler, Horst,Bermel, Wolfgang,Griesinger, Christian
, p. 596 - 601 (1986)
The signals of the aromatic carbon atoms in three tert-butylated 2-naphthols were assigned by the new two-dimensional NMR technique C-relayed H,C-COSY.The aplication of only one-bond coupling constants avoids any ambiguities in the assignment.A number of previous assignments had to be changed.The chemical shift values and one-bond C-C coupling constants have been correlated with electron densities and bond orders, respectively.
Reversible aromatic bromination induced by buttressing; 1-bromo- and 8-bromo-3,6-di-tert-butyl-2-methoxynaphthalene
Braddock, Christopher D,Tucker, Sonia C,Brown, John M
, p. 399 - 410 (2007/10/03)
Convenient syntheses of 3,6-di-tert-butylnaphthalen-2-ol and 3,3',6,6'-tetrakis-tert-butyl--2,2'-diol 1 are described.The methyl ether of the former is brominated most rapidly at the 1-position, similarly to 2-methoxynaphthalene.Unlike the parent comopound, there is a rapid proton-catalysed reversible reaction leading ultimately to the formation of 7-bromo-3,6-di-tert-butyl-2-methoxynaphthalene by an intermolecular route.This difference in reactivity is due to steric buttressing by the 3-tert-butyl group which destabilises the initial 1-bromo adduct towards 1-protonation leading to facilitated loss of bromonium ion; this explanation is in accord with a molecular mechanics analysis.The reactivity of the 1-bromo ether or its derivatives is strikingly different from that of its unsubstituted precursor, and exemplified by their responses to palladium-catalysed biaryl synthesis. - Keywords: binaphthyl; bromination; reversibility; Suzuki cross-coupling
