10240-08-1Relevant articles and documents
Photocatalytic hydrogen evolution of 1-tetralones to α-naphthols by continuous-flow technology
He, Xu,Zheng, Yi-Wen,Lei, Tao,Liu, Wen-Qiang,Chen, Bin,Feng, Ke,Tung, Chen-Ho,Wu, Li-Zhu
, p. 3337 - 3341 (2019)
Taking advantage of the synergy between photocatalysis and cobaloxime catalysis, the keto-enol radical cation of 1-tetralones becomes compatible with the transformation of various 1-tetralones into α-naphthols and H2 by virtue of the continuous-flow approach without any sacrificial oxidants under unusually mild conditions.
Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: Scope and limitations
Allen, Anna,Le Marquand, Paul,Burton, Ryan,Villeneuve, Karine,Tam, William
, p. 7849 - 7857 (2007)
(Chemical Equation Presented) Cationic rhodium(I)-catalyzed cyclodimerization of oxabenzonorbornadienes produced naphtho[1,2-b]-furan ring systems in a single step with excellent yields and excellent enantioselectivities. The effect of various Rh(I) catalysts, Ag(I) salts, solvents, and phosphine ligands on the yield and enantioselectivity of the reaction was investigated, and the scope and limitations of this reaction with various oxabicyclic alkenes were studied. Similar results were obtained with the azabenzonorbornadiene analogues, providing the corresponding cyclodimerization products in excellent yields and excellent enantioselectivities.
Isomerization of 7-oxabenzonorbornadienes into naphthols catalyzed by [RuCl2(CO)3]2
Ballantine, Melissa,Menard, Michelle L.,Tam, William
, p. 7570 - 7573 (2009)
(Chemical Equation Presented) Ruthenium-catalyzed isomerization of 7-oxanorbornadienes into naphthols was investigated. Among the various ruthenium catalysts tested, [RuCl2(CO)3]2 gave the highest yields in the isomerizati
Cu(OTf)2-catalyzed isomerization of 7-oxabicyclic alkenes: A practical route to the synthesis of 1-naphthol derivatives
Peng, Fangzhi,Fan, Baomin,Shao, Zhihui,Pu, Xuewei,Li, Penghui,Zhang, Hongbin
, p. 3043 - 3046 (2008)
Lewis acid catalyzed isomerization of 7-oxabicyclic alkenes into 1-naphthol derivatives in high yields (87-98%) under mild reaction conditions has been developed. The mechanism of this reaction is briefly postulated. Georg Thieme Verlag Stuttgart.
Yarboro,Karr
, p. 1141 (1959)
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Klemm,L.H. et al.
, p. 1480 - 1488 (1968)
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Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes
Hill, Jarvis,Tam, William
, p. 8309 - 8314 (2019)
The palladium/Lewis acid cocatalyzed ring-opening reaction of various C1-substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C1 substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained for electron-withdrawing groups. The presence of electron-donating alkyl groups leads to isomerization of the corresponding OBD to afford the substituted naphthol derivatives. Additionally, a mechanism for the formation of C2 regioisomeric ring-opened products has been proposed.
Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol
Bertozzi, Fabio,Pineschi, Mauro,Macchia, Franco,Arnold, Leggy A.,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 2703 - 2705 (2002)
An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of anti-stereoselectivity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).
Catalytic Alkylation of 1-Naphthol with Methanol
Agaev,Nazarova
, p. 558 - 560 (2003)
The reaction of 1-naphthol with methanol in the presence of mordenite catalysts was studied. The synthesis conditions ensuring high yields of methylnaphthols, methylnaphthalenes, or methoxynaphthalene were determined.
Site-selective Oxidative Dearomatization of Phenols and Naphthols into ortho-Quinols or Epoxy ortho-Quinols using Oxone as the Source of Dimethyldioxirane
Cabrera-Afonso, María J.,Carre?o, M. Carmen,Urbano, Antonio
supporting information, (2019/08/21)
A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho-quinols or epoxy ortho-quinols from a site-selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step. (Figure presented.).