Synthesis of 2,6-dioxabicyclo[3.3.0]octanes and 3,8-dioxabicyclo[4.4.0]dec-1(6)-enes by electrophilic cyclization of 3,4-dimethylene-1,6-hexanediols |
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| Authors: | M E Gurskii S B Golovin M O Dekaprilevich Yu T Struchkov Yu N Bubnov |
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| Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation;(2) A. N. Nemeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation |
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| Abstract: | 3,4-Dimethylene-1,6-hexane diols2 obtained by allylboration of ketones with 2,3-dimethylene-1,4-bis(dipropylboryl)butane1 undergo cyclization on treatment with I2/NaHCO3 to give 1,5-cis-di(iodomethyl)-2,6-dioxabicyclo3.3.0]octanes (4) and/or 3,8-dioxabicyclo4.4.0]dec-1(6)-enes (5). 4,4,9,9-Tetramethyl-3,8-dioxacyclodeca-1,6-dione (9) was synthesized by ozonolysis of bicyclic compound5b. The structure of compound5e was confirmed by X-ray diffraction analysis.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1308–1314, July, 1995.This study was financially supported by the Russian Foundation for Basic Research (Grant No. 94-03-18193) and the International Science Foundation (Grant No. M3Y000). |
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| Keywords: | allylboronation intramolecular iodocyclization tetrahydrofurans 3-methylenetetrahydrofurans 2 6-dioxabicyclo[3 3 0]octanes 3 8-dioxabicyclo[4 4 0]dec-1(6)-enes |
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