Phosphorus-Carbon Double Bonds by K. Dimroth

By K. Dimroth

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In eyclohexane/methanol the methylester 81b, also described by, Mach is obtained. OH 92 4 02 ,Sens a) R= H b) R = CH3 81 80 o 82 The analytical and spectroscopic data of the lower-melting compound are in accord with structure 82. We therefore suppose that in the first step addition of the singlet oxygen takes place at the C, position 4, and at the phosphorus of 24, leading to the endoperoxide 80. This intermediate, which we could not isolate, is then converted by hydrolysis or aleoholysis to 81a or 81b, or it rearranges to the endoxv-XS-ohosohinoxide 82.

4'-peroxy phosphinic acid 68.

A third electron is then transferred from the contact with the K - N a alloy, forming the paramagnetic radical trianion 6 7. 6-tris-pentadeuterophenyl-Xa-phosphorin. 6G) 66 67 Our interpretation is strengthened by the following observations: 1) Upon mixing equivalent amounts of separately prepared solutions of the radical cation 58 (ap = 23,2 Gauss) and the radical anion 65 (ap = 32,4 Gauss), the ESR signal disappears. 6-triphenyl-X3-phosphorin 22 can be seen in the UV spectrum. 2) If a solution of the radical trianion 67 (prepared by the K/Na method) is "titrated" with a solution of the Xa-phosphorin 22, then upon addition of one aliquot of 22 to 2 aliquots of 67 no ESR signal can be seen (formation of the dianion 66).

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