Decomposition of di-p-toluenesulfonyl-hydrazones Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/k643b4079

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  • Carbene chemistry
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  • Thermal decomposition of several di-p-toluenesulfonylhydrazones was studied. It was found that the carbene decomposition of tetramethyl-1,3-cyclobutanedione, di-p-toluenesulfonylhydrazone gave two products resulting from rearrangement. One was identified as 2,5-dimethyl-1,3,4-hexatriene. A tentative structure for the second was proposed. During the course of the study, a more convenient procedure for thermal decompositions was developed, involving the use of sodium hydride to prepare the salt and vacuum to aid in isolation of the products. The use of an alcohol to protonate the intermediate diazo compound was also studied. Two other di-p-toluenesulfonylhydrazones were decomposed under carbene conditions to give products derived entirely from hydrogen migration via a stepwise mechanism.
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  • File scanned at 300 ppi using Capture Perfect 3.0 on a Canon DR-9050C in PDF format. CVista PdfCompressor 5.0 was used for pdf compression and textual OCR.
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