Matches in SemOpenAlex for { <https://semopenalex.org/work/W2401622081> ?p ?o ?g. }
- W2401622081 endingPage "7446" @default.
- W2401622081 startingPage "7435" @default.
- W2401622081 abstract "Palladium-catalyzed cross-coupling reactions of 2-bromobenzaldehyde and 6-bromo-2,3-dimethoxybenzaldehyde with 4-methyl-1-naphthaleneboronic acid and acenaphthene-5-boronic acid gave corresponding o-naphthyl benzaldehydes. Corey–Fuchs olefination followed by reaction with n-BuLi led to various 1-(2-ethynylphenyl)naphthalenes. Cycloisomerization of individual 1-(2-ethynylphenyl)naphthalenes to various benzo[c]phenanthrene (BcPh) analogues was accomplished smoothly with catalytic PtCl2 in PhMe. In the case of 4,5-dihydrobenzo[l]acephenanthrylene, oxidation with DDQ gave benzo[l]acephenanthrylene. The dimethoxy-substituted benzo[c]phenanthrenes were demethylated with BBr3 and oxidized to the o-quinones with PDC. Reduction of these quinones with NaBH4 in THF/EtOH in an oxygen atmosphere gave the respective dihydrodiols. Exposure of the dihydrodiols to N-bromoacetamide in THF-H2O led to bromohydrins that were cyclized with Amberlite IRA 400 HO– to yield the series 1 diol epoxides. Epoxidation of the dihydrodiols with mCPBA gave the isomeric series 2 diol epoxides. All of the hydrocarbons as well as the methoxy-substituted ones were crystallized and analyzed by X-ray crystallography, and these data are compared to other previously studied BcPh derivatives. The methodology described is highly modular and can be utilized for the synthesis of a wide variety of angularly fused polycyclic aromatic hydrocarbons and their putative metabolites and/or other derivatives." @default.
- W2401622081 created "2016-06-24" @default.
- W2401622081 creator A5010134206 @default.
- W2401622081 creator A5026198726 @default.
- W2401622081 creator A5052221803 @default.
- W2401622081 creator A5073373934 @default.
- W2401622081 date "2015-07-21" @default.
- W2401622081 modified "2023-10-17" @default.
- W2401622081 title "Modular, Metal-Catalyzed Cycloisomerization Approach to Angularly Fused Polycyclic Aromatic Hydrocarbons and Their Oxidized Derivatives" @default.
- W2401622081 cites W1519992423 @default.
- W2401622081 cites W189344779 @default.
- W2401622081 cites W1964928139 @default.
- W2401622081 cites W1966598308 @default.
- W2401622081 cites W1967159419 @default.
- W2401622081 cites W1972850783 @default.
- W2401622081 cites W1977508291 @default.
- W2401622081 cites W1980918728 @default.
- W2401622081 cites W1983196555 @default.
- W2401622081 cites W1983209664 @default.
- W2401622081 cites W1989771566 @default.
- W2401622081 cites W1993547193 @default.
- W2401622081 cites W1996659121 @default.
- W2401622081 cites W1999940510 @default.
- W2401622081 cites W2000319560 @default.
- W2401622081 cites W2009972378 @default.
- W2401622081 cites W2011645864 @default.
- W2401622081 cites W2016878131 @default.
- W2401622081 cites W2020370687 @default.
- W2401622081 cites W2024985972 @default.
- W2401622081 cites W2029727778 @default.
- W2401622081 cites W2030668104 @default.
- W2401622081 cites W2030909050 @default.
- W2401622081 cites W2031109095 @default.
- W2401622081 cites W2035670524 @default.
- W2401622081 cites W2037866423 @default.
- W2401622081 cites W2038798777 @default.
- W2401622081 cites W2039431992 @default.
- W2401622081 cites W2042310701 @default.
- W2401622081 cites W2042915585 @default.
- W2401622081 cites W2046638467 @default.
- W2401622081 cites W2048910222 @default.
- W2401622081 cites W2050953612 @default.
- W2401622081 cites W2053365908 @default.
- W2401622081 cites W2057329486 @default.
- W2401622081 cites W2058129958 @default.
- W2401622081 cites W2059409127 @default.
- W2401622081 cites W2059951126 @default.
- W2401622081 cites W2060195575 @default.
- W2401622081 cites W2061130014 @default.
- W2401622081 cites W2064477578 @default.
- W2401622081 cites W2065091408 @default.
- W2401622081 cites W2065758000 @default.
- W2401622081 cites W2066472853 @default.
- W2401622081 cites W2068910849 @default.
- W2401622081 cites W2069175708 @default.
- W2401622081 cites W2069539698 @default.
- W2401622081 cites W2075288584 @default.
- W2401622081 cites W2075711854 @default.
- W2401622081 cites W2078505271 @default.
- W2401622081 cites W2080400999 @default.
- W2401622081 cites W2082438325 @default.
- W2401622081 cites W2082797262 @default.
- W2401622081 cites W2087652521 @default.
- W2401622081 cites W2088193717 @default.
- W2401622081 cites W2089473326 @default.
- W2401622081 cites W2090990681 @default.
- W2401622081 cites W2094129456 @default.
- W2401622081 cites W2095496033 @default.
- W2401622081 cites W2098120604 @default.
- W2401622081 cites W2103603843 @default.
- W2401622081 cites W2103785650 @default.
- W2401622081 cites W2106198369 @default.
- W2401622081 cites W2108830462 @default.
- W2401622081 cites W2110371196 @default.
- W2401622081 cites W2114869173 @default.
- W2401622081 cites W2115285962 @default.
- W2401622081 cites W2118093068 @default.
- W2401622081 cites W2135446807 @default.
- W2401622081 cites W2138104949 @default.
- W2401622081 cites W2148502720 @default.
- W2401622081 cites W2153157543 @default.
- W2401622081 cites W2155417227 @default.
- W2401622081 cites W2157933551 @default.
- W2401622081 cites W2161938380 @default.
- W2401622081 cites W2175728713 @default.
- W2401622081 cites W2273128310 @default.
- W2401622081 cites W2314362610 @default.
- W2401622081 cites W2316808493 @default.
- W2401622081 cites W2318468106 @default.
- W2401622081 cites W2323755609 @default.
- W2401622081 cites W2332232695 @default.
- W2401622081 cites W2332241575 @default.
- W2401622081 cites W2333827620 @default.
- W2401622081 cites W2346161654 @default.
- W2401622081 cites W2416295281 @default.
- W2401622081 cites W2949122803 @default.
- W2401622081 cites W2949310492 @default.
- W2401622081 cites W2949475634 @default.