Electron Acceptors of the Fluorene Series. 10.1 Novel Acceptors

J. Org. Chem. 2000, 65, 3053-3063

3053

Electron Acceptors of the Fluorene Series. 10.1 Novel Acceptors Containing Butylsulfanyl, Butylsulfinyl, and Butylsulfonyl Substituents: Synthesis, Cyclic Voltammetry, Charge-Transfer Complexation with Anthracene in Solution, and X-ray Crystal Structures of Two Tetrathiafulvalene Complexes Igor F. Perepichka,*,† Anatolii F. Popov,† Tatyana V. Orekhova,† Martin R. Bryce,*,‡ Alexander M. Andrievskii,§ Andrei S. Batsanov,‡ Judith A. K. Howard,‡ and Nikolai I. Sokolov| L. M. Litvinenko Institute of Physical Organic & Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk 340114, Ukraine, Department of Chemistry, University of Durham, Durham DH1 3LE, U.K., Stock Company “Center of International Cooperation and Service” (SC “CMESS”) Moscow 123100, Russian Federation, and Laboratory of Holography, Natural Faculty, University “Kievo-Mogilyanskaya Academy”, Kiev 254145, Ukraine Received November 19, 1999

2,4,5,7-Tetranitro-9-fluorenone (1b) reacts readily with n-butanethiol in dipolar aprotic solvents with selective substitution of nitro groups by butylsulfanyl groups in positions 2 and 7 (2, 3); the 2,5-isomer 4 was formed only as a minor product (