30964-01-3Relevant articles and documents
Carbon-carbon bond fission on oxidation of primary alcohols to carboxylic acids
Bekish, Andrei V.
scheme or table, p. 3082 - 3085 (2012/07/28)
α-Carbon-carbon bond cleavage is shown to be a general side reaction accompanying the oxidation of unbranched primary alcohols to the corresponding carboxylic acids using HNO3, CrO3/H2SO 4/H2O/acetone, CrO3/CH3COOH, PDC/DMF, H5IO6/CrO3, KMnO4/H +, KMnO4/HO-, NiCl2/NaClO, TEMPO/PhI(OAc)2. Therefore, the product formed is always contaminated with a carboxylic acid containing one carbon atom less. Systems such as PhI(OAc)2/TEMPO or H5IO6/CrO 3/CH3CN reduce to a minimum the content of this impurity. Temperature, the order of reagent addition, and additives such as oxalic acid or cerium salts produce a profound effect on the formation of the undesirable impurity during the Jones oxidation of primary alcohols.
STRUCTURES AND SYNTHESIS OF SEED-GERMINATION INHIBITORS FROM HIBISCUS ROSA-SINENSIS
Nakatani, Munehiro,Yamachika, Takashi,Tanoue, Takao,Hase, Tsunao
, p. 39 - 42 (2007/10/02)
Key Word Index - Hibiscus rosa-sinensis; Malvaceae; seed germination; inhibition; acetylenic acids; o-nitrophenyl selenide. 8-Nonynoic, 9-decynoic acids and their methyl esters were isolated for the first time as natural products from Hibiscus rosa-sinensis.They were inhibitors of the germination of lettuce seeds and were synthesized via o-nitrophenyl selenides.
Metamorphosis of Castor Oil to Insect Sex-pheromones and Useful Synthons
Ranganathan, S.,Maniktala, Vibha,Kumar, Raaj,Singh, G. P.
, p. 1197 - 1207 (2007/10/02)
The primary fragmentation products of Castor oil (1), namely, methyl undec-10-enoate (2) and sebacic acid (3) have been converted, using novel reactions and strategies into synthons of the type H-CC-(CH2)n-3-CH2OTHP (n=6=4; n=7=14; n=8=22; n=9=29).A surprisingly clean decarboxylative elimination of sebacic acid monoester gives methyl non-8-enoate (7), a synthon related to recefeiolide and a precursor to 4, the utility of which, has been illustrated with the synthesis of insect-pheromones of the species Grapholita molesta.Methyl dec-9-enoate (15) has been prepared by a novel and practical terminal ? to lower terminal ? degradation of 2.Compound 7 has been transformed via synthon 14 to the insect sex-pheromones of the species, Spodoptera frugiperda, Heliothis virescens and Paralobesia viteana in high yields and excellent stereochemical purity. 1-Tetrahydropyranyloxyundec-10-yne (22) readily prepared from 2, has been used to illustrate a new strategy in pheromone synthesis, namely, the use of coupling elements, leading to the preparation of bombykol in high yields and excellent stereochemical purity. 1-Tetrahydropyranyloxydodec-11-yne (29), already reported, has been transformed to vaccenic acid (30), the transposed ?-isomer of oleic acid, in good yields, thus demonstrating the use of acetylide synthons for the preparation of rare fatty acids also.