I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid

I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid

I. THE SYNTHESIS OF METHYLENECYCLOBUTANE FROM PENTAERYTHRITYL CHLORIDE A new method for preparing methylenecyclobutane is described in which the starting material is pentaerythrityl tetrachloride. Pentaerythrityl chloride is dechlorinated by zinc dust in the presence of sodium iodide and sodium car...

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Main Author: Winniford, Robert Stanley
Format: Others
Published: 1948
Online Access:https://thesis.library.caltech.edu/3941/1/Winniford_rs_1948.pdf
Winniford, Robert Stanley (1948) I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid. Master's thesis, California Institute of Technology. doi:10.7907/ZMYX-Z369. https://resolver.caltech.edu/CaltechETD:etd-10062005-083407 <https://resolver.caltech.edu/CaltechETD:etd-10062005-083407>
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spelling ndltd-CALTECH-oai-thesis.library.caltech.edu-39412019-12-22T03:08:17Z I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid Winniford, Robert Stanley I. THE SYNTHESIS OF METHYLENECYCLOBUTANE FROM PENTAERYTHRITYL CHLORIDE A new method for preparing methylenecyclobutane is described in which the starting material is pentaerythrityl tetrachloride. Pentaerythrityl chloride is dechlorinated by zinc dust in the presence of sodium iodide and sodium carbonate, using as solvent either diethylene glycol or acetamide. Reasonable yields are obtained. II. THE ATTEMPTED SYNTHESIS OF CYCLOBUTANONE A synthesis of cyclobutanone through treatment of the methylenecyclobutane-nitrogen trioxide addition compound, with alcoholic potassium hydroxide is not successful. The oxidation of methylenecyclobutane dibromide with potassium permanganate does not yield cyclobutanone. III. A REINVESTIGATION OF THE SYNTHESIS OF SPIROHEPTANEDICARBOXYLIC ACID An experiment is described in which two mols of malonic ester are condensed with one mol of pentaerythrityl chloride to form spiroheptanetetracarboxylic acid ester. The tetra acid is decarboxylated by heat to afford the dicarboxylic acid. The procedure is a modification of that described in the literature, whereby spiroheptanedicarboxylic acid is prepared from pentaerythrityl bromide. A parallel experiment in which pentaerythrityl bromide is condensed with malonic ester is also described. The yields are low in each case. 1948 Thesis NonPeerReviewed application/pdf https://thesis.library.caltech.edu/3941/1/Winniford_rs_1948.pdf https://resolver.caltech.edu/CaltechETD:etd-10062005-083407 Winniford, Robert Stanley (1948) I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid. Master's thesis, California Institute of Technology. doi:10.7907/ZMYX-Z369. https://resolver.caltech.edu/CaltechETD:etd-10062005-083407 <https://resolver.caltech.edu/CaltechETD:etd-10062005-083407> https://thesis.library.caltech.edu/3941/
collection NDLTD
format Others
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description I. THE SYNTHESIS OF METHYLENECYCLOBUTANE FROM PENTAERYTHRITYL CHLORIDE A new method for preparing methylenecyclobutane is described in which the starting material is pentaerythrityl tetrachloride. Pentaerythrityl chloride is dechlorinated by zinc dust in the presence of sodium iodide and sodium carbonate, using as solvent either diethylene glycol or acetamide. Reasonable yields are obtained. II. THE ATTEMPTED SYNTHESIS OF CYCLOBUTANONE A synthesis of cyclobutanone through treatment of the methylenecyclobutane-nitrogen trioxide addition compound, with alcoholic potassium hydroxide is not successful. The oxidation of methylenecyclobutane dibromide with potassium permanganate does not yield cyclobutanone. III. A REINVESTIGATION OF THE SYNTHESIS OF SPIROHEPTANEDICARBOXYLIC ACID An experiment is described in which two mols of malonic ester are condensed with one mol of pentaerythrityl chloride to form spiroheptanetetracarboxylic acid ester. The tetra acid is decarboxylated by heat to afford the dicarboxylic acid. The procedure is a modification of that described in the literature, whereby spiroheptanedicarboxylic acid is prepared from pentaerythrityl bromide. A parallel experiment in which pentaerythrityl bromide is condensed with malonic ester is also described. The yields are low in each case.
author Winniford, Robert Stanley
spellingShingle Winniford, Robert Stanley
I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid
author_facet Winniford, Robert Stanley
author_sort Winniford, Robert Stanley
title I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid
title_short I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid
title_full I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid
title_fullStr I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid
title_full_unstemmed I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid
title_sort i. synthesis of methylenecyclobutane from pentaerythrityl chloride. ii. the attempted synthesis of cyclobutane. iii. reinvestigation of the synthesis of spiroheptanedicarboxylic acid
publishDate 1948
url https://thesis.library.caltech.edu/3941/1/Winniford_rs_1948.pdf
Winniford, Robert Stanley (1948) I. Synthesis of methylenecyclobutane from pentaerythrityl chloride. II. The attempted synthesis of cyclobutane. III. Reinvestigation of the synthesis of spiroheptanedicarboxylic acid. Master's thesis, California Institute of Technology. doi:10.7907/ZMYX-Z369. https://resolver.caltech.edu/CaltechETD:etd-10062005-083407 <https://resolver.caltech.edu/CaltechETD:etd-10062005-083407>
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