The synthesis of conjugated diacetylene monomers for the fabrication of polymerized monolayer assemblies

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 11-14

  Mowery, Mark D ^a   Evans, Christine E ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYACETYLENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; POLYMERIZATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0031014735     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02262-9     Document Type: Article

References (19)

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12. Windows Material Safety Data Sheet Viewers Version 1.01 ; Aldrich Chemical Co. Inc.; Copyright 1992-1995.
13. Iodination of a terminal alkyne (Step A). n-Butyllithium is added to a solution of the terminal alkyne (30 mmol) in 250 ml hexane cooled in an ice bath. After 20 minutes, l .5 equivalents of solid iodine is added and the mixture is stirred for four hours. The solution is washed with a saturated aqueous sodium thiosulfate solution to remove residual iodine and the organic phase is collected and dried over sodium sulfate. The iodinated alkyne (product I) is recovered in greater than 90% yield by evaporation of the solvent. The product is used in the coupling reaction without further purification.
14. Chodkiewicz, W. Ann. Chim. 1957, 2, 819.
15. Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H.G. Ed.; Dekker; New York, 1969; p. 597.
16. 4 and extracted four times with diethyl ether. The combined extracts are dried over sodium sulfate. The product is purified by evaporating the solvent and recrystalizing the remaining solid from petroleum ether to produce a slightly yellow solid (product II) in yields ranging from 50-60% depending upon chain length.
17. Kabalka, G.W.; Varma, M.; Varma, R.S. J. Org. Chem. 1986, 51, 2386-2388.
18. 3, t, 3H).
19. -1): 2918 (CH asymm. stretch), 2850 (CH sym. stretch), 1472 (CH scissor), 716 (C-S stretch). Combustion Analysis: Calculated Found Product IV C H C H m=9,n=7 78.93% 11.04% 79.03% 11.32% m=9,n=11 79.93% 11.54% 79.80% 11.56% m=9,n=15 80.67% 11.91% 80.40% 11.81%