13651-14-4Relevant articles and documents
Identification of 2,2,7,8-Tetramethyl-1,2,3,4-tetrahydronaphthalene in Petroleum
Forster, Peter G.,Alexander, Robert,Kagi, Robert I.
, p. 274 - 276 (1989)
2,2,7,8-Tetramethyl-1,2,3,4-tetrahydronaphthalene, a proposed key intermediate in the degradation and aromatisation of triterpenoids of the oleanane skeletal-type, has been synthesized and identified in Cretaceous sediments and crude oils.
-
Smith,Spillane
, p. 2639,2641 (1940)
-
Structure and Selectivity in Anodic and Metal Ion Oxidations of Polyalkylbenzenes
Baciocchi, Enrico,Eberson, Lennart,Rol, Cesare
, p. 5106 - 5110 (1982)
Positional selectivity and the partition deuterium isotope effect (kH/kD) have been determined in the chemical and electrochemical side-chain oxidation of alkyl aromatics by using 5-R-hemimellitenes (R = H, t-Bu) and 1,3-dimethyl-2-(trideuteriomethyl)-5-tert-butylbenzene as the substrates.Considering also the already available data for isodurene, it has been found that the positional selectivity is strongly influenced by the substrate structure in the anodic and CAN-promoted oxidations, both reactions exhibiting a very similar pattern.In contrast, Co(OAc)3, selectivities do not correlate with those of the anodic oxidation but with the selectivities of the side-chain bromination promoted by NBS.These results have been interpreted by suggesting that, as in the anodic oxidations, CAN-induced reactions involve first the formation of a radical cation intermediate which then loses a proton to give a benzylic free radical in the selectivity-determining step.The data for Co(III) would instead suggest a mechanism involving a hydrogen atom transfer, but this conclusion cannot yet be considered definitive.No simple correlation exists between selectivity data and the kH/kD values.
Total syntheses of multicaulins via oxidative photocyclization of stilbenes
Seinti, Hatice,Burmaolu, Serdar,Altunda, Ramazan,Seen, Hasan
, p. 2134 - 2137 (2014/12/11)
The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6
Selective lithiation of 4- and 5-halophthalans
Garcia, Daniel,Foubelo, Francisco,Yus, Miguel
experimental part, p. 991 - 1005 (2010/10/03)
The reaction of 4- and 5-halophthalans 5 with lithium and a catalytic amount of DTBB at -78 °C leads to the formation of the corresponding functionalized organolithium intermediates 6 and 11, which by reaction with carbonyl compounds give, after hydrolysis, the expected substituted phthalans 8 and 13, respectively. When after reaction with the carbonyl compound the system is allowed to react at 0 °C, a second lithiation occur: A reductive opening of the heterocycle takes place with some regioselectivity leading to new organolithium intermediates 9 and 14/15 that by reaction with electrophiles lead, after hydrolysis, to polyfunctionalized molecules 10 and 16/17, respectively.
