The Journal of Organic Chemistry

Photodecomposition of the dianion of tetramethylcyclobutane-1, 3-dione bis (p-tosylhydrazone)

PK Freeman, RC Johnson

Index: Freeman,P.K.; Johnson,R.C. Journal of Organic Chemistry, 1969 , vol. 34, p. 1751 - 1759

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Abstract

Irradiation of the disodium salt of the di-ptosylhydrazone of tetramethylcyclobutane-l, 3-dione in methanol generates 2, 2, 4-trimethylpent-3-enal dimethyl acetal and 2, 2, 4-trirnethylpent- knal, accompanied by methyl 2, 2, 4-trimethylpent-3-enoate, which waa subsequently found to be due to an impurity of the mono-ptosylhydrazone of tetramethylcyclobutane-l, 3-dione in the starting material. The mechanism of decomposition is discussed.

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