30069-72-8Relevant academic research and scientific papers
Site-Selective C–C Cleavage of Benzocyclobutenones Enabled by a Blocking Strategy Using Nickel Catalysis
Guo, Jing-Hong,Hu, Ping,Lin, Xin-Cheng,Liu, Yu,Shi, Zhang-Jie,Song, Feijie,Tang, Tian-Mu,Wang, Bi-Qin,Zhao, Ke-Qing
, p. 19079 - 19084 (2021)
Controlling the chemo- and regioselectivity of transition-metal-catalyzed C?C activation remains a great challenge. The transformations of benzocyclobutenones (BCBs) usually involve the cleavage of C1?C2 bond. In this work, an unprecedented highly selective cleavage of C1?C8 bond with the insertion of alkynes is achieved by using blocking strategy via Ni catalysis, providing an efficient method for synthesis of 1,8-disubstituted naphthalenes. Notably, the blocking group could be readily removed after the transformation.
Nitrone Directing Groups in Rhodium(III)-Catalyzed C?H Activation of Arenes: 1,3-Dipoles versus Traceless Directing Groups
Xie, Fang,Yu, Songjie,Qi, Zisong,Li, Xingwei
supporting information, p. 15351 - 15355 (2016/12/06)
Functionalizable directing groups (DGs) are highly desirable in C?H activation chemistry. The nitrone DGs are explored in rhodium(III)-catalyzed C?H activation of arenes and couplings with cyclopropenones. N-tert-butyl nitrones bearing a small ortho subst
Interesting reactivity in the thermolysis and photolysis of 2,3-diphenyl-1-naphthol
Guzei, Ilia A.,Zimmerman, Howard E.,Shorunov, Sergey,Spencer, Lara C.
experimental part, p. 399 - 406 (2010/04/06)
2,3-Diphenyl-1-naphthol (1) undergoes two unexpected reactions under different conditions. Compound (1) was heated in DMSO-d6 and underwent a Pummerer type thermal reaction to give two isomeric products, 1-(methylthio)methoxy-2,3-diphenyl naphthol-d5 which crystallized in the space group P1 with a = 7.1610(9) A, b = 11.2795(15) A, c = 12.8905(17) A, α = 114.049(2)°, β = 96.589(2)°, and γ = 102.945(2)°, and 2-(methylthio)methyl-2,3-diphenyl 1(2H)-naphthalenone-d5 which crystallized in the space group P1 with a = 8.5981(5) A, b = 10.4374(6) A, c = 11.1078(6) A, α = 78.748(2)°, β = 67.709(2)°, and γ = 83.184(2)°. Photolysis (254 nm) of (1) resulted in 2,2',3,3'-tetraphenyl-1,1'-bi-2-naphthol which crystallized in the space group P21/c with a = 26.3616(11) A, b = 10.1707(4) A, c = 23.3376(9) A, and β = 99.034(2)°.
Organic photochemical rearrangements of triplets and zwitterions; mechanistic and exploratory organic photochemistry
Zimmerman, Howard E.,Suryanarayan, Vijay
, p. 4091 - 4102 (2008/02/13)
There has been some controversy about the mechanisms of reactions of enones and dienones. The question has been whether a zwitterion or diradical is involved as the intermediate. In the case of ground state species it has not been recognized that zwitterions may have diradical character. In triplet reactions there is the question of whether the rearrangements take place at the initial T1 stage or subsequently as S0 ground state zwitterions or diradicals. We now have some new rearrangements bearing on these questions. In some cases it is the triplet which rearranges, while in others it is the SO zwitterion. The zwitterion vs. diradical nature of the S0 species has been assessed by both experimental as well as theoretical means. Similarly, both experiment and computational theory have been used to determine at what stage the triplet rearrangements occur and to determine the characteristics of the rearranging species. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Metal-catalyzed cyclopropene rearrangements for benzannulation: Evaluation of an anthraquinone synthesis pathway and reevaluation of the parallel approach via carbene-chromium complexes
Semmelhack,Ho, Suzzy,Cohen,Steigerwald,Lee,Lee,Gilbert, Adam M.,Wutff, William D.,Ball, Richard G.
, p. 7108 - 7122 (2007/10/02)
The reaction of 3-arylcyclopropenes with Cr(CO)6 and Mo(CO)6 produces naphthols, in an example of metal-promoted benzannulation. Substituents at C- 3 (in addition to aryl) have a strong effect on the success of the process: 3-H deriv
Preparation of 1-naphthols from acetylenes and o-phthalaldehyde using low-valent tantalum and niobium
Kataoka,Miyai,Tezuka,Takai,Oshima,Utimoto
, p. 369 - 372 (2007/10/02)
Tantalum (or niobium)-alkyne complexes are produced by treatment of acetylenes with the low-valent tantalum (niobium) derived by zinc reduction of TaCl5 (NbCl5). Substituted 1-naphthols are prepared regioselectively by reaction of o-phthalaldehyde with the tantalum (or niobium)-alkyne complexes in good to excellent yield.
