Thianthrene as a source of the 1,2-benzene dianion

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7205-7207

  Yus, Miguel ^a   Foubelo, Francisco ^a   Ferrández, José V ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Cyclisation; Dianionic synthon; DTBB catalysed lithiation; Heterocycle reductive opening

Indexed keywords

4,4' DI TERT BUTYLBIPHENYL; ALKENE DERIVATIVE; ANION; BENZENE; BENZENE DERIVATIVE; CARBON DIOXIDE; CARBONYL DERIVATIVE; LITHIUM; PHTHALIDE DERIVATIVE; THIANTHRENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; GAS LIQUID CHROMATOGRAPHY; HYDROLYSIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

EID: 0037201178     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01661-1     Document Type: Article

References (38)

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2. For monographs, see: (a) Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995; (b) Handbook of Grignard Reagents; Silverman, G. S.; Rekita, P. E., Eds.; Marcel Dekker: New York, 1996; (c) Grignard Reagents New Developments; Richey, H. G., Jr., Ed.; J. Wiley and Sons: Chichester, 2000.
3. For monographs, see: (a) Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995; (b) Handbook of Grignard Reagents; Silverman, G. S.; Rekita, P. E., Eds.; Marcel Dekker: New York, 1996; (c) Grignard Reagents New Developments; Richey, H. G., Jr., Ed.; J. Wiley and Sons: Chichester, 2000.
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5. For monographs, see: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988; (b) Lithium Chemistry. A Theoretical and Experimental Overview; Sapse, A.-M.; von Ragué Schleyer, P., Eds.; J. Wiley and Sons: Chichester, 1995; (c) Bartsab, R.; Drost, C.; Klingebiel, U. In Synthetic Methods of Organometallic and Inorganic Chemistry; Herrmann, W. A., Ed.; G. Thieme Verlag: Stuttgart, 1996; Vol. 2, pp. 1-23; (e) Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002.
6. For monographs, see: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988; (b) Lithium Chemistry. A Theoretical and Experimental Overview; Sapse, A.-M.; von Ragué Schleyer, P., Eds.; J. Wiley and Sons: Chichester, 1995; (c) Bartsab, R.; Drost, C.; Klingebiel, U. In Synthetic Methods of Organometallic and Inorganic Chemistry; Herrmann, W. A., Ed.; G. Thieme Verlag: Stuttgart, 1996; Vol. 2, pp. 1-23; (e) Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002.
7. For monographs, see: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988; (b) Lithium Chemistry. A Theoretical and Experimental Overview; Sapse, A.-M.; von Ragué Schleyer, P., Eds.; J. Wiley and Sons: Chichester, 1995; (c) Bartsab, R.; Drost, C.; Klingebiel, U. In Synthetic Methods of Organometallic and Inorganic Chemistry; Herrmann, W. A., Ed.; G. Thieme Verlag: Stuttgart, 1996; Vol. 2, pp. 1-23; (e) Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002.
8. For reviews, see: (a) Maercker, A. In Ref. 2b, Chapter 11; (b) Foubelo, F.; Yus, M. Trends Org. Chem. 1998, 7, 1-26.
9. For reviews, see: (a) Maercker, A. In Ref. 2b, Chapter 11; (b) Foubelo, F.; Yus, M. Trends Org. Chem. 1998, 7, 1-26.
10. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
11. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
12. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
13. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
14. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
15. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
16. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
17. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
18. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
19. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
20. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
21. For the first account of this topic from our group, see: (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For reviews, see: (b) Yus, M. Chem. Soc. Rev. 1996, 25, 155-161; (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225-237; (d) Yus, M. Synlett 2001, 1197-1205; (e) Yus, M.; Ramón, D. J. Latv. J. Chem. 2002, 79-92. For mechanistic studies, see: (f) Yus, M.; Herrera, R. P.; Guijarro, A. Tetrahedron Lett. 2001, 42, 3455-3458; (g) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2000, 8, 2574-2584. For a polymer supported arene-catalysed version of this reaction, see: (h) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397-1400; (i) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron 1999, 55, 7017-7026; (j) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081-1083; (k) Yus, M.; Gómez, C.; Candela, P. Tetrahedron 2002, 58, 6207-6210. From a previous paper on this topic from our laboratory, see: (e) Yus, M.; Ramón, D. J.; Gómez, I. Tetrahedron 2002, 58, 5163-5172.
22. See, for instance: (a) Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1998, 39, 3303-3306; (b) Foubelo, F.; Yus, M. Tetrahedron Lett. 1999, 40, 743-746; (c) Lorenzo, E.; Alonso, F.; Yus, M. Tetrahedron Lett. 2000, 41, 1661-1665; (d) Foubelo, F.; Saleh, S. A.; Yus, M. J. Org. Chem. 2000, 65, 3478-3483; (e) Foubelo, F.; Yus, M. Tetrahedron Lett. 2000, 41, 5047-5051.
23. See, for instance: (a) Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1998, 39, 3303-3306; (b) Foubelo, F.; Yus, M. Tetrahedron Lett. 1999, 40, 743-746; (c) Lorenzo, E.; Alonso, F.; Yus, M. Tetrahedron Lett. 2000, 41, 1661-1665; (d) Foubelo, F.; Saleh, S. A.; Yus, M. J. Org. Chem. 2000, 65, 3478-3483; (e) Foubelo, F.; Yus, M. Tetrahedron Lett. 2000, 41, 5047-5051.
24. See, for instance: (a) Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1998, 39, 3303-3306; (b) Foubelo, F.; Yus, M. Tetrahedron Lett. 1999, 40, 743-746; (c) Lorenzo, E.; Alonso, F.; Yus, M. Tetrahedron Lett. 2000, 41, 1661-1665; (d) Foubelo, F.; Saleh, S. A.; Yus, M. J. Org. Chem. 2000, 65, 3478-3483; (e) Foubelo, F.; Yus, M. Tetrahedron Lett. 2000, 41, 5047-5051.
25. See, for instance: (a) Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1998, 39, 3303-3306; (b) Foubelo, F.; Yus, M. Tetrahedron Lett. 1999, 40, 743-746; (c) Lorenzo, E.; Alonso, F.; Yus, M. Tetrahedron Lett. 2000, 41, 1661-1665; (d) Foubelo, F.; Saleh, S. A.; Yus, M. J. Org. Chem. 2000, 65, 3478-3483; (e) Foubelo, F.; Yus, M. Tetrahedron Lett. 2000, 41, 5047-5051.
26. See, for instance: (a) Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1998, 39, 3303-3306; (b) Foubelo, F.; Yus, M. Tetrahedron Lett. 1999, 40, 743-746; (c) Lorenzo, E.; Alonso, F.; Yus, M. Tetrahedron Lett. 2000, 41, 1661-1665; (d) Foubelo, F.; Saleh, S. A.; Yus, M. J. Org. Chem. 2000, 65, 3478-3483; (e) Foubelo, F.; Yus, M. Tetrahedron Lett. 2000, 41, 5047-5051.
27. For a review, see: (a) Yus, M.; Foubelo, F. Rev. Heteroatom Chem. 1997, 17, 73-107. For a previous paper on this topic from our laboratory, see: (b) Yus, M.; Foubelo, F.; Ferrández, J. V. Chem. Lett. 2002, 726-727.
28. For a review, see: (a) Yus, M.; Foubelo, F. Rev. Heteroatom Chem. 1997, 17, 73-107. For a previous paper on this topic from our laboratory, see: (b) Yus, M.; Foubelo, F.; Ferrández, J. V. Chem. Lett. 2002, 726-727.
29. For reviews, see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181; (b) Nájera, C.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 67-96; (c) Nájera, C.; Yus, M. Curr. Org. Chem., in press. For a more general review, see: (d) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
30. For reviews, see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181; (b) Nájera, C.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 67-96; (c) Nájera, C.; Yus, M. Curr. Org. Chem., in press. For a more general review, see: (d) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
31. For reviews, see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181; (b) Nájera, C.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 67-96; (c) Nájera, C.; Yus, M. Curr. Org. Chem., in press. For a more general review, see: (d) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
32. For reviews, see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181; (b) Nájera, C.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 67-96; (c) Nájera, C.; Yus, M. Curr. Org. Chem., in press. For a more general review, see: (d) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435.
33. The formation of intermediates I and II was demonstrated by hydrolysis of both systems giving the expected compounds resulting from a lithium-hydrogen exchange (see Ref. 6b).
34. E reaction) or in a Barbier-type process (lithiation in the presence of the electrophile). For a monograph, see: (a) Blomberg, C. The Barbier Reaction and Related Processes; Springer: Berlin, 1993. For a review, see: (b) Alonso, F.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 397-436.
35. E reaction) or in a Barbier-type process (lithiation in the presence of the electrophile). For a monograph, see: (a) Blomberg, C. The Barbier Reaction and Related Processes; Springer: Berlin, 1993. For a review, see: (b) Alonso, F.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 397-436.
36. At the same time, dilithio 1,2-benzenedithiolate is formed which, after final protonation, was removed from the reaction products by acid-base extraction.
37. See, for instance: Yus M., Foubelo F., Ferrández J.V., Bachki A. Tetrahedron. 58:2002;4907-4915.
38. See, for instance: Almena J., Foubelo F., Yus M. Tetrahedron. 51:1995;3351-3364.