Reactions of p-benzoquinone and its derivatives with hydroxide and alkoxide ions (RO-:  R = H, Me, Et, i-Pr, PhCH2) in acetonitrile (MeCN) result in formation of the corresponding semiquinone radical anions accompanied by the formation of RO-substituted p-benzoquinones, which are the oxidized products of p-benzoquinones. Detailed product and kinetic analyses of the reactions have demonstrated that the RO-adduct anion of p-benzoquinone is a real electron donor and that RO- is acting as a very strong base or nucleophile rather than a one-electron reductant in an aprotic solvent, such as MeCN. Similarly, the reaction of C60 with methoxide anion (MeO-) in benzonitrile (PhCN) results in formation of C60 •-. Spectroscopic and kinetic studies also indicate that a methoxy adduct anion of C60 is an actual electron donor and that MeO- is acting as a very strong base or nucleophile rather than an electron donor in PhCN.

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COMMUNICATIONS[7] Selected physical and spectral data of DTEDT 1 a : M.p. 197 C (decomp.); IR (KBr): i. = 3059. 1504. 1283, 1261, 805cm-'; UV (CHCI,): i.,,,, (Igc) = 402 (4.54). 345 (4.46).283(4.23) nm; 'H NMR(90 MHz.CS2/C,D,,25"C.TMS): r S = 6 0 4 (~. 4 H ) . 5.69is.ZH): MS(70eV):m/s:406[M+].