1.2.3.4- Tetrahydro-l -naphthyl

Tetrahydro-l-naphthyl hydroperoxide See 1,2,3,4-Tetrahydro-l-naphthyl hydroperoxide Lithium tetrahydroaluminate... 

Tetralin hydroperoxide (1,2,3,4-tetrahydro-l-naphthyl hydroperoxide) and 9,10-dihydroanthracyl-9-hydroperoxide were prepared by oxidizing the two hydrocarbons and purified by recrystallization. Commercial cumene hydroperoxide was purified by successive conversions to its sodium salt until it no longer increased the rate of oxidation of cumene at 56°C. All three hydroperoxides were 100% pure by iodometric titration. They all initiated oxidations both thermally (possibly by the bi-molecular reaction, R OOH + RH — R O + H20 + R (33)) and photochemically. The experimental conditions were chosen so that the rate of the thermally initiated reaction was less than 10% of the rate of the photoreaction. The rates of chain initiation were measured with the inhibitors 2,6-di-ter -butyl-4-methylphenol and 2,6-di-fer -butyl-4-meth-oxyphenol. None of the hydroperoxides introduced any kinetically first-order chain termination process into the over-all reaction. 

Tetralin Hydroperoxide. See in Vol 8, P207-L under 1,2,3,4-Tetrahydro-l-Naphthyl Hydroperoxide and the following Addril Refs J.S. McDonald J.S. Owens, Investigation of Tetralin Explosion , NAA-SR-4803, Atomics Intrnl, Canoga Park, Contract AT (1 l-l)-GEN-8 (1960) [An expln in a Na-tetralin heat exchanger is reported as being caused by the unforeseen formation of a-tetralin hydroperoxide. The decompn ° hydroperoxide to Oi-tetralone... 

Tetrahydro-l-naphthyl hydroperoxide, 3306 Tetrahydro-l,4-oxazine, see Morpholine, 1652... 

It is found that esters which are known to undergo unimolecular alkyl-oxygen heterolysis will alkylate hydrogen peroxide and alkyl hydroperoxides (3, 4) for example, sodium 1,2,3,4-tetrahydro-l-naphthyl phthalate in 90% hydrogen peroxide rapidly yields 1,2,3,4-tetrahydro-l-naphthyl hydroperoxide ... 

The substrate scope of the DKR protocol above was extended to include a wide range of primary amines [89]. Functional groups tolerated include fluorine, bromine, nitrile, nitrate, and trifluoromethyl. Aliphatic amines and more sterically hindered substrates were also obtained in high yields and ee values. The method was found applicable with both isopropenyl acetate and dibenzyl carbonate as acyl donors. For 18 different substrates, the corresponding enantiomericafly pure products were obtained in high to excellent yields (70-95%) and with high to excellent ee values (93 to >99%). The chemoenzymatic DKR protocol was also applied to the synthesis of norsertraline, from readily available 1,2,3,4-tetrahydro-l-naphthyl-amine. Norsertraline is cmrently in clinical trials for the treatment of central nervous system (CNS) disorders. 

---