Organic Monolayers as Nucleation Sites for Epitaxial Growth: II. Synthesis of ω-N-Pyrrolo-Functionalized n-Dialkyl Disulfide

REFERENCES

• Ulman , A. 1991 . An Introduction to Ultrathin Organic Films; From Langmuir Blodgett to Self-Assembly , Boston, MA : Academic Press .
   Google Scholar
• Bain , C. D. , Troughton , E. B. , Tao , Y.-T. , Evall , J. , Whitesides , G. M. and Nuzzo , R. G. 1989 . J. Am. Chem. Soc. , 111 : 321
   Web of Science ®Google Scholar
• Kim , T. and Crooks , R. M. 1994 . Tetrahedron Letters , 35 : 9501
   Web of Science ®Google Scholar
• Sayre , C. N. and Collard , D. M. 1995 . Langmuir , 11 : 302
   Web of Science ®Google Scholar
• Kowalik , J. , Tolbert , L. , Ding , Y. , Bottomley , L. , Vogt , K. and Kohl , P. 1993 . Synth. Met. , 55 : 1171
   Web of Science ®Google Scholar
• Dubois , L. H. and Nuzzo , R. G. 1992 . Annu. Rev. Phys. Chem. , 43 : 437
   Web of Science ®Google Scholar
• Ricco , A. J. , Crooks , R. M. , Xu , C. and Allred , R. E. 1994 . Interfacial Design and Chemical Sensing , ACS Symposium Series 561 Edited by: Mallouk , T. E. and Harrison , D. J. Washington, D. C. : American Chemical Society . Ch. 23
   Google Scholar
• Kumar , A. and Whitesides , G. M. 1993 . Appl. Phys. Lett. , 261 : 449
   Google Scholar
• Yamamoto , Y. , Nishihara , H. and Aramaki , K. 1993 . J. Electrochem. Soc. , 140 : 436
   Web of Science ®Google Scholar
• Willicut , R. J. and McCarley , R. L. 1995 . Langmuir , 11 : 296
   Web of Science ®Google Scholar
• Chidsey , C. E. D. 1991 . Science , 314 : 13
   Google Scholar
• A white solid; mp 38–40 °C; 1H NMR (360 MHz, CDCl3) d 7.80 (d, J = 8.3 Hz, 4 H), 7.35 (d, J = 8.3 Hz, 4 H), 4.05 (t, J = 6.6 Hz, 4 H), 2.68 (t, J = 7.3 Hz, 4 H), 2.45 (s, 6 H), 1.75–1.55 (m, 8 H), 1.45–1.15 (m, 28 H); 13C NMR (90 MHz, CDCl3) d 144.57, 133.27, 129.76, 127.84, 70.65, 39.14, 29.38 (C × 2), 29.31(C × 2), 29.17, 28.88, 28.79, 28.47, 25.29, 21.60
   Google Scholar
• Hobbs , C. F. , McMillin , C. K. , Papadopoulos , E. P. and Vanderwerf , C. A. 1962 . J. Am. Chem. Soc. , 84 : 43
   Web of Science ®Google Scholar
• Heaney , H. and Ley , S. V. 1974 . Org. Synth. , 54 : 58
   Google Scholar
• Bocchi , V. , Casnati , G. , Dossena , A. and Villani , F. 1976 . Synthesis , : 414
   Google Scholar
• Barco , A. , Benetti , S. and Pollini , G. P. 1976 . Synthesis , : 124
   Google Scholar
• Guida , W. C. and Mathre , D. J. 1980 . J. Org. Chem. , 45 : 3172
   Web of Science ®Google Scholar
• Rubottom , G. M. and Chabala , J. C. 1972 . Synthesis , : 566
   Google Scholar
• General procedure for alkylation: A solution of pyrrole (1.69 g, 25.2 mmol) in HMPA (56 mL) was flushed with nitrogen and cooled to 0 °C. To the solution was added with stirring sodium hydride (538 mg, 22.4 mmol; previously washed with hexane to remove mineral oil) over a period of 10 min. The reaction mixture was stirred at room temperature for 5h and then cooled to 0 °C again. 4 (4.0 g, 5.60 mmol) was added and the resulting mixture was allowed to room temperature and stirred at room temperature for 12 h. The mixture was diluted with water (50 mL) and extracted with diethyl ether (3 × 60 mL). The combined organic layers were washed with water (2 × 50 mL) anddried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure and purified by chromatography on silica gel (80 g, 10:1 hexane/diethyl ether as a eluent) to afford the product as a pale yellow oil (1.73 g, 60%). 1H NMR (360 MHz, CDCl3) d 6.63 (dd, J = 2.1, 2.1 Hz, 4 H), 6.13 (dd, J = 2.1, 2.1 Hz, 4 H), 3.86 (t, J = 7.2 Hz, 4 H), 2.70 (t, J = 7.3 Hz, 4 H), 1.80–1.50 (m, 8 H), 1.50–1.20 (m, 28 H); 13C NMR (90 MHz, CDCl3) d 120.43,107.74, 49.61, 39.19, 31.56, 29.73, 29.45 (C × 2), 29.44, 29.20 (C × 2), 29.19, 28.50, 26.76; Anal. Calcd for C15H26NS: C, 71.37; H, 10.38. found: C, 71.26; H, 10.84
   Google Scholar
• Wurm , B. D. , Brittain , S. T. and Kim , Y.-T. submitted to Langmuir
   Google Scholar