Synthetic And Solvolytic Studies in the Bismethanonaphthalene System
Synthetic And Solvolytic Studies in the Bismethanonaphthalene System
Timberlake, John Foushee
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Anal.: Calcd. for C H 0.,: C, 70.55; H, 9.31 Found: C, 70.61; H f 9.32. ~) f. 9 7 Preparation of 12 , 12-dimethoxytetracyclo [6 . 2 . 1 . 1 ' .0 ' ]- dodec-11-yl p-bronobenzenesulfonate (55)-OBs A solution of 1.3 g (5.5 mmol.) of (55_) -OH and 3.0 g (12 mmol.) of p-bromobenzenesulf onyl chloride in 75 ml of 44 precooled pyridine was maintained at 10 °C for 24 hrs. This solution was poured into 300 ml of ice/water and extracted with 2 x 250 ml of ether. The combined ether layers were Ill washed ...with 400 ml of 3 _N hydrochloric acid, dried with anhydrous magnesium sulfate, filtered, and the ether re- moved under vacuum to give essentially a quantitative yield of crude (_55)-OBs. Recrystallization from benzene gave white prisms, m. p. 200.5 - 202.5 °C. The infrared spectrum (KBr) contained the following absorption bands: 2850 (m) , 1570 (m) , 1350 (s), 1190 (s), 960 (s) , 880 (s) , and 740 (s) cm" 1 . The Hnmr spectrum (CDCl-J contained the following resonances: 6 7.76 (aa'bb' quartet, 4; aromatic); 5.2 8 (broad s, 1; H, , ) ; 3.20 (s, 6; OCH.) ; and 1.1 - 2.2 (m, 14).
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