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Synthesis of 2-cyclobuten-1-ylphosphonates by the thermal cyclization of 1,3-butadienylphosphonates

Journal Article · · J. Gen. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:7005393
Heating (1-alkyl(aryl)-3-tert-butyl-chloro-1,3-butadienyl)phosphonic dichlorides leads to electrocyclic thermal cyclization with the formation of (1-alkyl(aryl)-3-tert-butyl-2-chloro(methylthio)-2-cyclobuten-1-yl)phosphonic dichlorides. It was shown that the replacement of a chlorine atom by an alkylthio group in a 1,3-alkadienylphosphonic dichloride does not influence the course of the reaction, but the replacement of one of the protons of the terminal =CH/sub 2/ group of the original diene by a chlorine atom makes butadiene-cyclobutene conversion impossible under analogous conditions; the replacement of a chlorine atom in the phosphonic dichloride grouping by phenyl makes cyclization more difficult. The PMR spectra were determined on a Tesla BS-497 spectrometer (100 MHz) with the use of hexamethyldisiloxane as standard. /sup 31/P chemical shifts were determined by the /sup 31/P NMR method on a spectrometer with a working frequency of 16.2 MHz.
OSTI ID:
7005393
Journal Information:
J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 57:7; ISSN JGCHA
Country of Publication:
United States
Language:
English