92241-45-7Relevant academic research and scientific papers
Asymmetric dihydroxylation of a meso-symmetric cyclic diene using AD-mix reagents: A new enantiocontrolled route to conduritol E
Takano,Yoshimitsu,Ogasawara
, p. 54 - 57 (1994)
The asymmetric dihydroxylation of two symmetric cyclohexa-1,3-diene derivatives, including a meso-symmetric substrate, has been investigated for the first time using the Sharpless AD-mix reagents. Although cyclohexa-1,3- diene itself showed unsatisfactory
Electron transfer catalyzed [2 + 2] cycloreversion of benzene dimers
Reddy, Devi,Wiest, Olaf,Hudlicky, Tomas,Schapiro, Valeria,Gonzalez, David
, p. 2860 - 2863 (2007/10/03)
The catalysis of the [2 + 2] cycloreversion of the anti-o,o'-benzene dimer 1 and the syn-o,o'naphthalene-benzene dimer 2 through thermal and photoinduced electron transfer is studied using experimental and computational methods. The reaction of the radical cations formed by electron transfer is at least 105 times faster than the thermal background reaction. It is demonstrated that the photoinduced electron transfer catalyzed reaction proceeds via an electron transfer sensitized pathway and that the observed inverse secondary deuterium isotope effect of 0.91 ± 0.02 on the reaction is due to the equilibrium isotope effect on the electron transfer step. The relevance of these findings on the mechanism of the electron transfer catalyzed [2 + 2] cycloreversion of the biologically important cis,syn- cyclobutane-thymine dimer is also discussed.
?-Facial diastereoselectivity in the Diels-Alder reactions of cis-cyclohexa-3,5-diene-1,2-diol and derivatives with N-phenylmaleimide
Gillard, James R.,Burnell, D. Jean
, p. 1296 - 1307 (2007/10/02)
N-Phenylmaleimide undergoes Diels-Alder cycloaddition predominantly to the face of cis-cyclohexa-2,4-diene-1,2-diol (3) syn to the oxygen functions.Derivatization can be used to alter the ?-facial diastereoselectivity in a synthetically useful manner.The
Chemistry of Benzene-Anthracene Cyclodimers
Yang, Nien-chu C.,Chen, Ming-Jang,Chen, Peter
, p. 7310 - 7315 (2007/10/02)
Synthesis of the formal s + 4?s> and s + 2?s> adducts of benzene and anthracene (1 and 2) has made possible the observation of features on the potential-energy surfaces that govern Woodward-Hoffmann-allowed and -forbidden cycloreversions.The thermal dissociation of 1 is not chemiluminescent in spite of favorable kinetic and thermodynamic parameters, and its photochemical dissociation yields excited anthracene in very high efficiency (ΦAn* = 0.80).The enthropy of activation in the thermal dissociation of 2 is negative, and the photochemical dissociation of 2 yields excited anthracene in low but appreciable efficiency (ΦAn* = 0.08).Comparision of these data clearly demonstrates orbital symmetry control of both the ground- and excited-state reactions.
