Derivatives of isocamphoric acid, decomposition of isodihydroaminocampholytic acid with nitrous acid . o-camphoric anhydride. The evidence furnished by the formation ofd-campholytic acid as described above leaves no doubt on thispoint, however . The lactone proved to be a new compound. When pure it was awaxy solid melting at 114 -115° and having a specific rotation,( ) = °. These constants show it to be 1-campholytolactone The discrepancy of four degrees in the two melting points isnot so great as it would appear. Potter and Noyes obtained themelting point of 118-119° for d-campholytolacto
Derivatives of isocamphoric acid, decomposition of isodihydroaminocampholytic acid with nitrous acid . o-camphoric anhydride. The evidence furnished by the formation ofd-campholytic acid as described above leaves no doubt on thispoint, however . The lactone proved to be a new compound. When pure it was awaxy solid melting at 114 -115° and having a specific rotation,( ) = °. These constants show it to be 1-campholytolactone The discrepancy of four degrees in the two melting points isnot so great as it would appear. Potter and Noyes obtained themelting point of 118-119° for d-campholytolactone only after re-peated recrystallizations . The small quantity of 1-campholytolac-tone with which the writer worked made numerous recrystallizations impossible. A sample of fairly pure d-campholytolactone gave amelting point of 114-115°. A mixture of this sample of d-campho-lytolactone with 1-campholytolactone gave the same melting point 0 3114-115 . This agrees with Blanc who evidently prepared r-campho- 1 . Ann. 316, 227. 2. Kindly given the writer by Mr. R. S. Potter. 3. Bull . (3) 25, d-campholytolactone 1-campholytolactone r 118-119°, (o()D= ° - 114-lltf5 , (<X) = -8 M 2 45 lytolactone and found it had the same melting point (121°) as1 Tiemann found for the d-campholytolactone. On hydrolysis 1-campholytolactone gave a hydroxy-acid havinga specific rotation, ( &\ )^4° = °, and m. p. = 117 - 118°.This shows the acid to be 1-cis-dihydrohydroxycampholytic acid. H2C Ho O H3CN /OH H3 C-C-OH3 K xC02H d-cis-dihydrohydroxycampho-lytic acid = °, (o<)D= ° H2C H2C H-0X yCH3 H3C-C-CH3 H02C^ XH 1-cis-d ihydrohydroxycampho-lytic acid = 117-llff , (<*)D= 1 . Eerichte 33, 2938 . The 1-campholytolactone is formed from isodihydroaminocampho-lytic acid by a Walden inversion on the tertiary asymmetric carbonatom just as d-trans-dihydrohydroxycampholytic acid is formed fromdihydrcaminocampholytic acid. In the former case, how
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