Dipotassium Hydrogen Phosphate Powder Catalyzed Synthesis of Alkyl 2-(2-Alkoxy-2-oxoethyl)dinaphtho[2,1-d:1,2-f][1,3]-dioxepin-2-Carboxylates from Stabilized Phosphorus Ylides in Solvent-Free Conditions |
| |
| Authors: | Ali Ramazani Issa Amini Abdolhossain Massoudi |
| |
| Affiliation: | 1. Chemistry Department , Zanjan University , Zanjan , Iran;2. Chemistry Department , Peyam Noor University of Abhar , Abhar , Iran;3. Chemistry Department , Peyam Noor University of Mashhad , Mashhad , Iran;4. Chemistry Department , Peyam Noor University of Mashhad , Mashhad , Iran |
| |
| Abstract: | The protonation of the highly reactive 1:1 intermediates, produced in the reaction of triphenylphosphine and dialkyl acetylenedicarboxylates, by 1,1-binaphthyl-2,2′-diol leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction to produce the corresponding stabilized phosphonium ylides. Dipotassium hydrogen phosphate powder was found to catalyze the conversion of the stabilized phosphonium ylides to alkyl 2-(2-alkoxy-2-oxoethyl)dinaphtho[2,1-d:1,2-f][1,3]-dioxepin-2-carboxylates under solvent-free conditions using microwave (0.6 KW, 3 min) and thermal (100°C, 60 min) conditions. |
| |
| Keywords: | 1,1-binaphthyl-2,2′-diol dipotassium hydrogen phosphate Michael addition acetylenic esters vinyltriphenylphosphonium salt microwave irradiation |
|
|
