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Volumn 65, Issue 7, 2000, Pages 2243-2245

[(3-Cyanopropyl)dimethylsilyl]acetylene, a polar analogue of (trimethylsilyl)acetylene: Synthesis and applications in the preparation of monoprotected bisacetylenes

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; COPPER; IODINE DERIVATIVE; PALLADIUM; TRIMETHYLSILYL DERIVATIVE;

EID: 0142131984     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991746m     Document Type: Note
Times cited : (48)

References (27)
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    • WILEY-VCH: Weinheim
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    • For the use of macrocycles based on phenylacetylene structures as host molecules; see for example: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 946. (e) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
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    • For the use of macrocycles based on phenylacetylene structures as host molecules; see for example: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 946. (e) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
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    • For the use of macrocycles based on phenylacetylene structures as host molecules; see for example: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 946. (e) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
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    • For the use of macrocycles based on phenylacetylene structures as host molecules; see for example: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 946. (e) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
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    • Anderson, H.L.1    Sanders, J.K.M.2
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    • For the use of macrocycles based on phenylacetylene structures as host molecules; see for example: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 946. (e) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
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    • During the coupling reaction, the aromatic bromide does not act as a protective group in the common sense, it has not to be transformed into a reactive group prior to the subsequent step. In general, the aryl bromide is reactive under the coupling conditions which are used, but remains unaffected as long as aryl iodide remains in the reaction mixture. Therefore, two regioselective coupling reactions can be performed in a one-pot reaction: Höger, S. Liebigs Ann./Recueil 1997, 273.
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    • For the use of the bromo-iodo selectivity in the preparation of well-defined molecular objects; see also: (a) Diercks, R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1986, 25, 266. (b) Goldfinger, M. B.; Swager, T. M. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35 (1), 274. (c) Bradshaw, J. D.; Guo, L.; Tessier, C. A.; Youngs, W. G. Organometallics 1996, 15, 2582. (d) Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
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    • 84985616441 scopus 로고
    • For the use of the bromo-iodo selectivity in the preparation of well-defined molecular objects; see also: (a) Diercks, R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1986, 25, 266. (b) Goldfinger, M. B.; Swager, T. M. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35 (1), 274. (c) Bradshaw, J. D.; Guo, L.; Tessier, C. A.; Youngs, W. G. Organometallics 1996, 15, 2582. (d) Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
    • (1994) Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) , vol.35 , Issue.1 , pp. 274
    • Goldfinger, M.B.1    Swager, T.M.2
  • 18
    • 0001370396 scopus 로고    scopus 로고
    • For the use of the bromo-iodo selectivity in the preparation of well-defined molecular objects; see also: (a) Diercks, R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1986, 25, 266. (b) Goldfinger, M. B.; Swager, T. M. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35 (1), 274. (c) Bradshaw, J. D.; Guo, L.; Tessier, C. A.; Youngs, W. G. Organometallics 1996, 15, 2582. (d) Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
    • (1996) Organometallics , vol.15 , pp. 2582
    • Bradshaw, J.D.1    Guo, L.2    Tessier, C.A.3    Youngs, W.G.4
  • 19
    • 0032543064 scopus 로고    scopus 로고
    • For the use of the bromo-iodo selectivity in the preparation of well-defined molecular objects; see also: (a) Diercks, R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1986, 25, 266. (b) Goldfinger, M. B.; Swager, T. M. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35 (1), 274. (c) Bradshaw, J. D.; Guo, L.; Tessier, C. A.; Youngs, W. G. Organometallics 1996, 15, 2582. (d) Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1285
    • Tobe, Y.1    Utsumi, N.2    Nagano, A.3    Naemura, K.4


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