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Organic Lab Reactions 177

Organic Lab Reactions 177 - 226 226 177 45,47 55 182 cf(o...

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172 THE FORMATION OF CYCLIC KETONES . TABLE XI SOME CTCLIZATIONS WITH STANNIC CHLOBIDE ON THE FREE ACIDS 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. Acids Submitted to Cyclization ' p-Phenylpropionic add a,5jdimethyl-2-isopropyl- 5-methyl-2-isopropyl- y-Phenylbutyric acid 3-methoxy- P-1-Naphthylpropionic acid fl-'ir-Naphihylpropionic acid y-1-Naphthylbutyric acid a,i8-cyclopentano- 5-methoxy- 6-methoxy- •Y-2-Naphthylbutyric acid /Vy-dimethyl-6-methoxy- 6-methoxy-5-methyl- y-2-Anthrylbutyi~ic acid y-1-Phenanthrylbutyric acid •y-3-Phenan(hrytt>utyrii; acid a-methyl- l-methyl-7-isopropyl- y-3-PyrenylbiUyric acid a-methyl- Yield? of Ketones (a) 69% (6) 90% 85-90% (c) 45% 32% 70% (d) 13% W 40% 68% 70% 72% 34-77% 65% 75% 29% 49% 37% 80% Reference 139 139 225 35 219 226 208 98 227 226 177 228
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Unformatted text preview: 226 208 98 227 226 177 228 56 41 45,47 55 182; cf. 181 81 81 (o) Cydisation process repeated twice on recovered acid. (&) Calculated from acid consumed (about one-half). (c) Ring closure in two directions to give mainly perinaphthenone resulting from dehydrogenation of the normal cyclization product perinaphthanone, and a small amount of 4,6-benihydrindone-l. (d) Toluene used as a solvent. (e) Abnormal cyclization; gives variable results (see p. 175). "» Peak and Robinson, J. Chem. Soc., 1937, 1581. » M Hoch, BuU. soc. chim. [5] 5, 264 (1938). "'Butenandt and Schramm, Ber., 68, 2083 (1985). •*• Hill, Short, and Higginbottom, J. Chem. Soc., 19»6, 317....
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