3153-74-0Relevant academic research and scientific papers
Synthesis of (±)-kuwanon v and (±)-dorsterone methyl ethers via Diels-Alder reaction
Chee, Chin Fei,Lee, Yean Kee,Buckle, Michael J.C.,Rahman, Noorsaadah Abd
, p. 1797 - 1799 (2011/04/26)
The mulberry Diels-Alder adducts, the pentamethyl ethers of kuwanon V 1a and dorsterone 2a were synthesised via a biomimetic intermolecular [4+2] cycloaddition reaction between a highly electron-rich dienophile and a Lewis acid sensitive diene derived fro
Solvent-free iodination of organic molecules using the I 2/urea-H2O2 reagent system
Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
, p. 699 - 707 (2008/03/27)
Introduction of iodine under solvent-free conditions into several aromatic compounds activated toward electrophilic functionalisation was found to proceed efficiently using elemental iodine in the presence of a solid oxidiser, the urea-H2O2 (UHP) adduct. Two types of iodo- functionalisation through an electrophilic process were observed: iodination of an aromatic ring, and side-chain iodo-functionalisation in the case of arylalkyl ketones. Two reaction routes were established based on the required substrate: iodine: oxidiser ratio for the most efficient iodo-transformation, and the role of UHP was elucidated in each route. The first, requiring a 1: 0.5: 0.6 stoichiometric ratio of substrate to iodine to UHP, followed the atom economy concept in regard to iodine and was valid in the case of aniline (1a), 4-t-Bu-phenol (3), 1,2-dimethoxy benzene (5a), 1,3-dimethoxy benzene (5b), 1,2,3-trimethoxy benzene (7a), 1,2,4-trimethoxy benzene (7b), 1,3,5-trimethoxy benzene (7c), 1-indanone (11a) and 1-tetralone (11b). The second reaction route, where a 1: 1: 1 stoichiometric ratio of substrate: I2: UHP was needed for efficient iodination, was suitable for side-chain iodo-functionalisations of acetophenone (1c) and methoxy-substituted acetophenones. Moreover, addition of iodine to 1-octene (13a) and some phenylacetylenic derivatives (15a, 15b) was found to proceed efficiently without the presence of any oxidiser and solvent at room temperature. This journal is The Royal Society of Chemistry.
