Untersuchungen über pflanzliche Fisch‐ und Insektengifte. II. 2. Mitteilung über Rotenon, den physiologisch wirksamen Bestandteil der Derris elliptica

The Determination of the Structure of Rotenone.

“…Like isotubaic acid, isorotenone is not readily reduced by catalytic hydrogenation. On cleavage with alcoholic alkali, isotubaic acid is obtained instead of tubaic acid (45,4,11).…”

“…It is of special importance that with the reductive cleavage of the oxide ring of the benzofuran system an asymmetric center is lost (15). If this reductive cleavage is associated with a reaction involving the loss of the asymmetric centers of the dihydro--pyrone system, the resulting compounds are inactive (4,15). Tetrahydromethylderritol (methyldihydroderritolic acid) (XXVI) and tetrahydrodehydrorotenone (dehydrodihydrorotenonic acid) (XXXII) are, for example, inactive (15).…”

“…Derritol methyl ether is oxidized by hydrogen peroxide at the carbonyl group to homoasaronic acid. 4 Tetrahydromethylderritol (XXVI) has been synthesized from tetrahydrotubanol (III) and homoasaronic acid (XX) by condensation with zinc chloride (50). The derritols are easily dehydrated (3,41) and the resulting anhydroderritols which contain the grouping XXVII are also…”

Alkyl and Arysulfonyl Derivatives of Ortho-Aminophenols

“…11 Zincke, J. prakt. Chem.,[2] 61, 563 (1900).12 In the use of this method it was found that the yield of product was influenced noticeably by the amount of ilitrite and the temperature, as shown in TableII. In the experiments indicated one-half a gram molecular proportion of the dibromocresol was dissolved in a suitable amount of glacial acetic acid, and the reaction completed by the use of different amounts of sodium nitrite-at the temperatures"indicated.…”

“…This paper contains important references to other work. 2 Lankelma and Knauf, ibid,, S3, 309 (1931). 3 Raiford and Lankelma, ibid., 47, 1111 (1925).…”