39171-65-8Relevant academic research and scientific papers
Phenalenannulations: Three-Point Double Annulation Reactions that Convert Benzenes into Pyrenes
Alabugin, Igor V.,Dos Santos, Nikolas R.,Hanson, Kenneth,Hu, Chaowei,Kawade, Rahul Kisan,Lin, Xinsong,Watson, Noelle
supporting information, p. 14352 - 14357 (2020/07/20)
3-Point annulations, or phenalenannulations, transform a benzene ring directly into a substituted pyrene by “wrapping” two new cycles around the perimeter of the central ring at three consecutive carbon atoms. This efficient, modular, and general method for π-extension opens access to non-symmetric pyrenes and their expanded analogues. Potentially, this approach can convert any aromatic ring bearing a -CH2Br or a -CHO group into a pyrene moiety. Depending upon the workup choices, the process can be directed towards either tin- or iodo-substituted product formation, giving complementary choices for further various cross-coupling reactions. The two-directional bis-double annulation adds two new polyaromatic extensions with a total of six new aromatic rings at a central core.
GLYCOSIDASE INHIBITORS
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Page/Page column 105, (2014/10/15)
Compounds of formula (I) wherein X1, X2, W, R1 to R5, L and m have the meaning according to the claims, are glucosidase inhibitors, and can be employed, inter alia, for the treatment of Alzheimer's disease.
Paracyclophanes. Part 58 [1]. On the use of the stilbene-phenanthrene photocyclization in [2.2]paracyclophane chemistry
Hopf,Hucker,Ernst
, p. 947 - 969 (2008/09/17)
The application of the stilbene→phenanthrene photocyclization to [2.2]paracyclophane chemistry has been investigated. For the model system 4-styryl[2.2]paracyclophane (2) to [2.2]phenanthrenoparacyclophane (3) the reaction allows the introduction of alkyl substituants in the 6-, 7-, 8- and 9-position of the phenanthrene moiety. However, when the substituent in the 9-position (bay area of phenanthrene nucleus) becomes too large, viz. tert-butyl, no ring closure is observed anymore. The side products of the process (ring cleavage products of the cyclophane core such as 9 and 10) have been characterized for the first time. Extension of the condensed deck is possible leading to PAH-phanes as demonstrated by the preparation of the chrysenophanes 45 and 60; the cyclization to novel helicenophanes such as 50 also takes place without difficulties. In the case of 1,2-di(4-[2.2] paracyclophanyl)ethene (63) the triply-layered hydrocarbon 65 is produced on irradiation in small amounts.
Asymmetric approaches to 2-hydroxymethylquinuclidine derivatives
Lygo,Crosby,Lowdon,Wainwright
, p. 2795 - 2810 (2007/10/03)
Highly enantio- and diastereoselective routes to 2- hydroxymethylquinuclidines have been developed. Key steps involve the use of Sharpless dihydroxylation or Sharpless epoxidation to introduce the asymmetry with high stereocontrol, and formation of the quinuclidine ring systems via cyclisation of epoxy amines.
Triplet Intermediates in Cis-Trans Photoisomerization of 3-Chrysenylethylenes
Karatsu, Takashi,Hiresaki, Tatsuro,Arai, Tatsuo,Sakuragi, Hirochika,Tokumaru, Katsumi,Wirz, Jakob
, p. 3355 - 3362 (2007/10/02)
The effect of substitution of 3-chrysenyl group (Ar) on unsaturated double bonds in their triplet sensitized isomerization was investigated for Ar-CH=CH-R, R = tBu (BC) and Ph (SC) by means of stationary irradiations, laser flash photolyses, and MO calculations.Both olefins undergo mutual isomerization between their cis- and trans-isomers.However, BC has a unique triplet energy surface with two decay funnels at the planar trans (3t*) and twisted (3p*) conformations, which are in equilibrium with each other; 3t* undergoes either unimolecular decay to the ground-state trans isomer or triplet energy transfer to the cis isomer (quantum chain process) and 3p* decays to the ground state to give the cis and trans isomers.Tn 1 absorptions observed for BC and SC are mainly attributed to 3t* and 3p*, respectively, on the basis of semiempirical MO calculations.The populations at 3t* and 3p* are estimated.
