Synthetic And Solvolytic Studies in the Endo, Exo-Bismethanonapthalene [sic] System
Synthetic And Solvolytic Studies in the Endo, Exo-Bismethanonapthalene [sic] System
Wallace, Benjamin
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2 . 1 . 1 ' .0 ' ] - dod ec- 4 - en- 11-yl-p-me thy 1 benzene sulfonate (69 ) -OTs A 0.124 gram (0.344 mmoles) sample of (69) -OTs was dissolved in 10 mL 0.02879 N sodium acetate in acetic acid containing 1% acetic anhydride. This mixture was placed in a volumetric flask, sealed and heated at 35°C for 35 hours. The flask was cooled to room temperature and the mixture poured into 100 mL of ice water. The aqueous mix- ture was extracted with 4 x 50 mL of pentane. The pentane extractions were comb...ined and washed with 2 x 50 mL of water, 2 x 50 mL of 10% aqueous sodium carbonate, and fi- nally 50 mL of water. The pentane phase was then dried over anhydrous potassium carbonate, filtered, and the pentane removed under reduced pressure to yield 0.058 grams of product. The infrared spectrum (NaCl, neat) contained only one carbonyl absorption at 1710 cm . The Hnmr spectrum reveals that the mixture contains approximately 85% of the acetate ( 7JL) -OAc and 15% of the corresponding tosylate (71^) -OAc.
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