Organic Lab Reactions 173

Organic Lab Reactions 173 - 8 'Q^o 2 cX)...

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168 THE FORMATION OF CYCLIC KETONES TABLE X—Continued SOME CYCLIZATIONS WITH STILFTJRIC ACID Acids Submitted to Cyclization a,a-dimethyl- a,7-dimethyl- <*,6-dimethyl- 7,6-dimethyl- 0,6-dimethyl- 6,7-dimethyl- 7-ethyl-6-methyl- 7-ethyl-6-isopropyl- 6-isopropyl- a-methyl- /3-methyl- 6-methyl- 7-methyl-6-isopropyl- 5,6,7,8-tetrahydro- 5,6,7,8-tetramethyl- a, j3, Y-trimethyl- j3,7,6-trimethyl- a,7,6-trimethyl- 7,6,7-trixjttethyl- l,2-Dihydrophenanthryl-4^acetic add y-2-Phmanthrylbutyric add 9,10-dihydro- y-3-Phenanthrylbutyric add 4b,5,6,7,8,8a,9,10-octahydr<H y-9-PhenanthrylbiUyric add 1,2,3,4,5,6,7,8-octahydro- l,2-Benzanthracene-5-acetic add l',2',3',4',l,2,3,4,5;6,7,8-dodecahydro- y-1-Pyrenylhutyric add 3,4,5,8,9,10-hexahydro- V-Naphthylmethyl-2-benzoic add
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Unformatted text preview: 8 'Q^o 2 cX) 2',7'-dimethoxy-Yields of KetoneS 80% 60% 50% 80% 50% 60% 75% 70% 00 25% 75% 69% 70% 40% 60% 30% # $ 75% 69% 29% (J) 97% 97% Reference 209 210 210 213- 210 210 214 214 210 193 210 213 213 15 27 27 215 215 215 35 46 58 46 216 217 216 80 218 218 (a) Double cyclization. (6) Mixture. (c) Heating unnecessary. (d) Crude ketone. (e) Pure ketoue. (f) Sulfurio-acetic acid mixture used for cyclization. (a) Dimethyl ester used for cyclization. (h) Mixture of da and trans isomers. (i) Variable results. U) Yield baaed on keto acid. (*) 9% acid recovered. (0 Seven-membered ring produced. [References to table on next page,]...
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