9,10-Dialkyl phenanthrenes

Polycyclic hydrocarbons.5 Perhydrogenation of 2,7-dialkyl-9,10-dihydro-phenanthrenes (1) with Pd/C as catalyst at 200° under pressures of 120-170 atm. results in the all-trans-perhydrophenanthrenes (2). A similar hydrogenation (Pd/C, HC104) converts 2,6-dialkylnaphthalenes (3) into trans-dialkyldecalins (4). 

Successive double deprotonation-alkylation of the dithioacetal 150 has also been performed in a one-pot procedure159-161 and used in cyclization processes for the preparation of indoles160 and the phenanthrene nucleus161. The dialkylation has been performed with primary alkyl iodides and bromides without additives. The cyclic sulfate 153 has been acy-lated by means of compound 151 and, after further deprotection of the thioacetal moiety, transformed into the corresponding 2-deoxy-D-arabinohexopyranose 154 (Scheme 43)162. 

S1097>. Reactions of phenanthrene-9,10-imine (20 R = H) with nucleophiles like NaN3 or RSCN under phase-transfer conditions gives compounds (62) and (63) respectively <84JHC1597>, while (20 R = C1) undergoes an unusual transformation to 9,10-phenanthroquinone dialkyl monoacetal (64) in a silver-promoted reaction (Scheme 23) <84JHC1593>. 

The coupling has to be performed in this way because McMurry coupling of dibromodiacylbiphenyl 83 proceeds with dehalogenation. Halogenation of the resulting 9,10-dialkyl(diaryl)phenanthrenes 84 occurs at the 3 and 6 positions so providing a route to the poly(3,6-phenanthrylene)s 85 (Scheme 37). 

Compounds of the type R2AIX (X = H, halogen, OR, SR, NR2) are usually strongly associated, the bond between two aluminum atoms being formed only by the substituents. The degree of association of such compounds depends on the nature of the substituents on the aluminum, and steric factors often play an important part. Dialkyl alanes, R2A1H, in benzene solution are trimeric, irrespective of the alkyl groups bonded to aluminum 103, 247). Some, such as di-l-alkyl aluminum hydrides, are also trimeric in phenanthrene at 100°C (307) ... 

Diels-Alder reactions, 133, 135 epoxidation, 69-72, 516 grafting on polyethylene, 462 hydroformylation, 44 hydrogenation, 41, 42 isomerization catalysts, 133, 484 isomerization during polymerizations, 484 isomerization kinetics, 484 isopropyl alcohol radical reaction, 207 MA copolymerization, 532, 534, 541 Michael reactions, 63-66 nitrone adducts, 224, 225 olefin copolymerization, 288 olefin ene reactions, 162 phenanthrene adducts, 181 plasticizers use, 14 production—synthesis, 14, 78-81 radical copolymerization, 270, 275-277, 307, 315, 317, 333, 345, 365, 379 radical polymerization, 239, 264, 287 reaction with allyl alcohol, 46 reaction with sodium bisulfite, 53 styrene copolymerization, 365, 483 tetraalkyl methylenediphosphonate adduct, 66 transesterification, 46 /7-xylylene copolymerization, 359 dialkyl stannyl, PVC stabilizer, 275 diaryl, synthesis from MA, 80 pyridinium, betaine intermediate, 216... 

For the separation of Ci—C4 dialkyl sulfides and alkyl benzyl sulfides the following stationary phases have been employed (20) silicone oil 7,8-benzoquinoline 5,6-benzoquinoline 2,4-dimethyl-7,8-benzoquinoline and phenanthrene Apiezon M and polymethylphenylsiloxane have also been used (21). 

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