Reducible Nanoscale Molecular Rods Based on Diacetylene - Linked Poly ( pheny 1 thio ) - Substituted
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چکیده
[6] G. Jaousen, A. Meyer, J. Am. chem. SOC. l975,97,4667-4672. [7] 31P NMR (109 MHz, [DJDMSO, H,PO,): theinitial species: 6 = 32.0-34.0, 27.5-29.5, 27.3 (s); after addition of iPr,NH (0.4equiv based on Pd): 6 = 27.5-29.5, 27.8 (s), 27.3 ( s ) . [8] For this experiment 4-A MS powder was dried at 300 "C for 8 h under vacuum (< 0.05 Torr) to prevent contamination by water; otherwise, a lower deuterium content (55%) resulted. We thank Dr. Masahiro Terada for suggesting this procedure. [9J The by-products were a-deuterated (to 70 %) a-(trimethylsilylmethyl)tetralone (4%, 81 % ee ) , a-hydroxy-a-methyltetralone (6%. 0 % ee), and 8-methyltetrahydro-%-naphthol ( lo%, 0% er) [lo] Enantiomeric excesses were determined by HPLC on CHIRALCEL OD-H for 2b-e and by capillary GLC on CP-chirasil-DEX CB for 2f and Zg. The configurations were assigned by comparing optical rotations with literature values: Zb: M. Murata, M. Nakajima, K. Koga, J Chem. SOC. Chem. Commun. 1990, 1657-1658; 2c: T. Yasukata, K. Koga, Tetrahedron: Asymmetrj~ 1993, 4, 3538; 2e: G. Berti, B.Macchia, F. Macchia, L. Menti, J Chem. SOC. C 1971, 3371-3375; 2g: A. I. Meyers, D. R. Williams, G. W. Erickson. S. White, M. Druelinger, J. Am. Chem. SOC. 1981,103,3081 -3087. The configurations of 2d and 2f, though not yet determined, were assigned based on the similarity of the values. chromatography on neutral silica gel.
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