A highly efficient synthesis of 1-alkylidene-1,3-dihydroisobenzofurans and 3-alkylidene isobenzofuran-1 (3H)-ones(phthalides) through palladium- copper catalysis using acetylenic carbinols as synthons

Synlett

Volumn , Issue 4, 1999, Pages 456-458

  Khan, M Wahab ^a   Kundu, Nitya G ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Acetylenic carbinols; Isobenzofurans; Palladium catalysis; Phthalides

Indexed keywords

COPPER; ISOBENZOFURAN DERIVATIVE; METHANOL; PALLADIUM; PHTHALIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032920005     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2639     Document Type: Article

References (55)

1. On study leave from Bangladesh University of Engineering and Technology, Dhaka, Bangladesh.
2. Traxler, P.;Gruner, J.; Auden, J. A. L. J. Antibiot., 1977, 30 289; Rommele, G.; Traxler, P.; Werli, W., J. Antibiot., 1983, 36, 1539; Van Middlesworth, F.; Olmstead, M. N.; Schmatz, D.; Bartizal, R.; Fromtling, R.; Bills, G.; Nolstadt, K.; Honeycult, S.; Zweernik, M.; Garrity, G.; Wilson, K. J. Antibiot., 1991, 44, 45; Kaneto, R.; Chiba, H.; Agematu, H.; Shibamoto, N.; Yoshioka, T.; Nishada, H.; Okamoto, M. J. Antibiot., 1993, 46, 247.
3. Traxler, P.;Gruner, J.; Auden, J. A. L. J. Antibiot., 1977, 30 289; Rommele, G.; Traxler, P.; Werli, W., J. Antibiot., 1983, 36, 1539; Van Middlesworth, F.; Olmstead, M. N.; Schmatz, D.; Bartizal, R.; Fromtling, R.; Bills, G.; Nolstadt, K.; Honeycult, S.; Zweernik, M.; Garrity, G.; Wilson, K. J. Antibiot., 1991, 44, 45; Kaneto, R.; Chiba, H.; Agematu, H.; Shibamoto, N.; Yoshioka, T.; Nishada, H.; Okamoto, M. J. Antibiot., 1993, 46, 247.
4. Traxler, P.;Gruner, J.; Auden, J. A. L. J. Antibiot., 1977, 30 289; Rommele, G.; Traxler, P.; Werli, W., J. Antibiot., 1983, 36, 1539; Van Middlesworth, F.; Olmstead, M. N.; Schmatz, D.; Bartizal, R.; Fromtling, R.; Bills, G.; Nolstadt, K.; Honeycult, S.; Zweernik, M.; Garrity, G.; Wilson, K. J. Antibiot., 1991, 44, 45; Kaneto, R.; Chiba, H.; Agematu, H.; Shibamoto, N.; Yoshioka, T.; Nishada, H.; Okamoto, M. J. Antibiot., 1993, 46, 247.
5. Traxler, P.;Gruner, J.; Auden, J. A. L. J. Antibiot., 1977, 30 289; Rommele, G.; Traxler, P.; Werli, W., J. Antibiot., 1983, 36, 1539; Van Middlesworth, F.; Olmstead, M. N.; Schmatz, D.; Bartizal, R.; Fromtling, R.; Bills, G.; Nolstadt, K.; Honeycult, S.; Zweernik, M.; Garrity, G.; Wilson, K. J. Antibiot., 1991, 44, 45; Kaneto, R.; Chiba, H.; Agematu, H.; Shibamoto, N.; Yoshioka, T.; Nishada, H.; Okamoto, M. J. Antibiot., 1993, 46, 247.
6. Tang, J.; Zhang, Y.; Hartman, T. G.; Rosen, R. T.; Ho, C. T. J. Agric. Food Chem., 1990, 38, 1937; Wassenhove, F.; Dirinck, P.; Vulsteke, G.; Schamp, N. Hort. Sci., 1990, 25, 556; Pushan, W.; Xuangliag, G.; Yixiong, W.; Fukuyama, Y.; Miura, I.; Sugawara, M. Phytochemistry, 1984, 23, 2033; Manske, R. H. F. Can. J. Res., 1938, 8, 142.
7. Tang, J.; Zhang, Y.; Hartman, T. G.; Rosen, R. T.; Ho, C. T. J. Agric. Food Chem., 1990, 38, 1937; Wassenhove, F.; Dirinck, P.; Vulsteke, G.; Schamp, N. Hort. Sci., 1990, 25, 556; Pushan, W.; Xuangliag, G.; Yixiong, W.; Fukuyama, Y.; Miura, I.; Sugawara, M. Phytochemistry, 1984, 23, 2033; Manske, R. H. F. Can. J. Res., 1938, 8, 142.
8. Tang, J.; Zhang, Y.; Hartman, T. G.; Rosen, R. T.; Ho, C. T. J. Agric. Food Chem., 1990, 38, 1937; Wassenhove, F.; Dirinck, P.; Vulsteke, G.; Schamp, N. Hort. Sci., 1990, 25, 556; Pushan, W.; Xuangliag, G.; Yixiong, W.; Fukuyama, Y.; Miura, I.; Sugawara, M. Phytochemistry, 1984, 23, 2033; Manske, R. H. F. Can. J. Res., 1938, 8, 142.
9. Tang, J.; Zhang, Y.; Hartman, T. G.; Rosen, R. T.; Ho, C. T. J. Agric. Food Chem., 1990, 38, 1937; Wassenhove, F.; Dirinck, P.; Vulsteke, G.; Schamp, N. Hort. Sci., 1990, 25, 556; Pushan, W.; Xuangliag, G.; Yixiong, W.; Fukuyama, Y.; Miura, I.; Sugawara, M. Phytochemistry, 1984, 23, 2033; Manske, R. H. F. Can. J. Res., 1938, 8, 142.
10. Friedrichsen, W. Advances in Heterocyclic chemistry, 1980, 26, 135; Wiersum, U. E. Aldrichimica Acta, 1981, 14, 53; Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Letters, 1991, 32, 4761; Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Letters, 1995, 36, 9285; Takeshita, H.; Yan, Y. Z.; Kato, N.; Mori, A.; Nozoe, T. Tetrahedron Letters, 1995, 36, 5195; Konig, B. M.; Friedrichsen, W. Tetrahedron Letters, 1987, 28, 4279.; Rodrigo, R. Tetrahedron, 1988, 29, 2093.
11. Friedrichsen, W. Advances in Heterocyclic chemistry, 1980, 26, 135; Wiersum, U. E. Aldrichimica Acta, 1981, 14, 53; Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Letters, 1991, 32, 4761; Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Letters, 1995, 36, 9285; Takeshita, H.; Yan, Y. Z.; Kato, N.; Mori, A.; Nozoe, T. Tetrahedron Letters, 1995, 36, 5195; Konig, B. M.; Friedrichsen, W. Tetrahedron Letters, 1987, 28, 4279.; Rodrigo, R. Tetrahedron, 1988, 29, 2093.
12. Friedrichsen, W. Advances in Heterocyclic chemistry, 1980, 26, 135; Wiersum, U. E. Aldrichimica Acta, 1981, 14, 53; Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Letters, 1991, 32, 4761; Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Letters, 1995, 36, 9285; Takeshita, H.; Yan, Y. Z.; Kato, N.; Mori, A.; Nozoe, T. Tetrahedron Letters, 1995, 36, 5195; Konig, B. M.; Friedrichsen, W. Tetrahedron Letters, 1987, 28, 4279.; Rodrigo, R. Tetrahedron, 1988, 29, 2093.
13. Friedrichsen, W. Advances in Heterocyclic chemistry, 1980, 26, 135; Wiersum, U. E. Aldrichimica Acta, 1981, 14, 53; Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Letters, 1991, 32, 4761; Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Letters, 1995, 36, 9285; Takeshita, H.; Yan, Y. Z.; Kato, N.; Mori, A.; Nozoe, T. Tetrahedron Letters, 1995, 36, 5195; Konig, B. M.; Friedrichsen, W. Tetrahedron Letters, 1987, 28, 4279.; Rodrigo, R. Tetrahedron, 1988, 29, 2093.
14. Friedrichsen, W. Advances in Heterocyclic chemistry, 1980, 26, 135; Wiersum, U. E. Aldrichimica Acta, 1981, 14, 53; Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Letters, 1991, 32, 4761; Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Letters, 1995, 36, 9285; Takeshita, H.; Yan, Y. Z.; Kato, N.; Mori, A.; Nozoe, T. Tetrahedron Letters, 1995, 36, 5195; Konig, B. M.; Friedrichsen, W. Tetrahedron Letters, 1987, 28, 4279.; Rodrigo, R. Tetrahedron, 1988, 29, 2093.
15. Friedrichsen, W. Advances in Heterocyclic chemistry, 1980, 26, 135; Wiersum, U. E. Aldrichimica Acta, 1981, 14, 53; Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Letters, 1991, 32, 4761; Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Letters, 1995, 36, 9285; Takeshita, H.; Yan, Y. Z.; Kato, N.; Mori, A.; Nozoe, T. Tetrahedron Letters, 1995, 36, 5195; Konig, B. M.; Friedrichsen, W. Tetrahedron Letters, 1987, 28, 4279.; Rodrigo, R. Tetrahedron, 1988, 29, 2093.
16. Friedrichsen, W. Advances in Heterocyclic chemistry, 1980, 26, 135; Wiersum, U. E. Aldrichimica Acta, 1981, 14, 53; Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Letters, 1991, 32, 4761; Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Letters, 1995, 36, 9285; Takeshita, H.; Yan, Y. Z.; Kato, N.; Mori, A.; Nozoe, T. Tetrahedron Letters, 1995, 36, 5195; Konig, B. M.; Friedrichsen, W. Tetrahedron Letters, 1987, 28, 4279.; Rodrigo, R. Tetrahedron, 1988, 29, 2093.
17. Cundaswamy, N. E.; Mclean, D. B. Can. J. Chem., 1972, 50, 3028; Scartoni, V.; Fiaschi, R.; Catalano, S.; Morelli, I.; Marsilli, A. J. Chem. Soc., Perkin Trans I, 1979, 1547; Broadhurst, M. J.; Hassall, C. H. J. Chem. Soc., Perkin Trans I, 1982, 2227; Bates, M. A.; Sammes, P. G.; Thomson, G. A. J. Chem, Soc., Perkin Trans I, 1988, 3037.
18. Cundaswamy, N. E.; Mclean, D. B. Can. J. Chem., 1972, 50, 3028; Scartoni, V.; Fiaschi, R.; Catalano, S.; Morelli, I.; Marsilli, A. J. Chem. Soc., Perkin Trans I, 1979, 1547; Broadhurst, M. J.; Hassall, C. H. J. Chem. Soc., Perkin Trans I, 1982, 2227; Bates, M. A.; Sammes, P. G.; Thomson, G. A. J. Chem, Soc., Perkin Trans I, 1988, 3037.
19. Cundaswamy, N. E.; Mclean, D. B. Can. J. Chem., 1972, 50, 3028; Scartoni, V.; Fiaschi, R.; Catalano, S.; Morelli, I.; Marsilli, A. J. Chem. Soc., Perkin Trans I, 1979, 1547; Broadhurst, M. J.; Hassall, C. H. J. Chem. Soc., Perkin Trans I, 1982, 2227; Bates, M. A.; Sammes, P. G.; Thomson, G. A. J. Chem, Soc., Perkin Trans I, 1988, 3037.
20. Cundaswamy, N. E.; Mclean, D. B. Can. J. Chem., 1972, 50, 3028; Scartoni, V.; Fiaschi, R.; Catalano, S.; Morelli, I.; Marsilli, A. J. Chem. Soc., Perkin Trans I, 1979, 1547; Broadhurst, M. J.; Hassall, C. H. J. Chem. Soc., Perkin Trans I, 1982, 2227; Bates, M. A.; Sammes, P. G.; Thomson, G. A. J. Chem, Soc., Perkin Trans I, 1988, 3037.
21. Natelson, S.; Pearl, A. J. Am. Chem. Soc, 1936, 58, 2448;
22. (b) Smith, J. G.; Wikman, R. T. Tetrahedron, 1974, 30 2603;
23. Smith, J. G.; Welankiwar, S. S.; Shantz, B. S.; Lai, E. H.; Chu, N. G. J Org. Chem., 1980, 45, 1817;
24. Makhlouf, M. A.; Rickborn, B. J. Org. Chem., 1981, 46, 2734;
25. (e) Villemin, D.; Goussu, D. Heterocycles, 1989, 29, 1255;
26. (f) Weingarten, M. D.; Padwa, A. Tetrahedron Letters, 1995, 36, 4717.
27. Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun., 1993, 86; Kundu, N. G.; Pal, M.; Nandi, B. J. Chem. Soc., Perkin Trans I, 1998, 561 and references cited therein.
28. Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun., 1993, 86; Kundu, N. G.; Pal, M.; Nandi, B. J. Chem. Soc., Perkin Trans I, 1998, 561 and references cited therein.
29. Heck, R. F. Org. React., 1982, 27, 345; in Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991; Tsuji, J. Palladium Reagents and Catalysts, Wiley and Sons, 1995; Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2; Negishi, E.; Coperet, C. Ma, S. Liou, S. Y.; Liu, F. Chem. Revs., 1996, 365; Mallern, J. L.; Fiaud, J. C.; Legros, J. Y. Hand book of Palladium- Catalyzed Organic Reactions, Academic Press, London, 1997.
30. Heck, R. F. Org. React., 1982, 27, 345; in Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991; Tsuji, J. Palladium Reagents and Catalysts, Wiley and Sons, 1995; Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2; Negishi, E.; Coperet, C. Ma, S. Liou, S. Y.; Liu, F. Chem. Revs., 1996, 365; Mallern, J. L.; Fiaud, J. C.; Legros, J. Y. Hand book of Palladium- Catalyzed Organic Reactions, Academic Press, London, 1997.
31. Heck, R. F. Org. React., 1982, 27, 345; in Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991; Tsuji, J. Palladium Reagents and Catalysts, Wiley and Sons, 1995; Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2; Negishi, E.; Coperet, C. Ma, S. Liou, S. Y.; Liu, F. Chem. Revs., 1996, 365; Mallern, J. L.; Fiaud, J. C.; Legros, J. Y. Hand book of Palladium- Catalyzed Organic Reactions, Academic Press, London, 1997.
32. Heck, R. F. Org. React., 1982, 27, 345; in Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991; Tsuji, J. Palladium Reagents and Catalysts, Wiley and Sons, 1995; Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2; Negishi, E.; Coperet, C. Ma, S. Liou, S. Y.; Liu, F. Chem. Revs., 1996, 365; Mallern, J. L.; Fiaud, J. C.; Legros, J. Y. Hand book of Palladium- Catalyzed Organic Reactions, Academic Press, London, 1997.
33. Heck, R. F. Org. React., 1982, 27, 345; in Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991; Tsuji, J. Palladium Reagents and Catalysts, Wiley and Sons, 1995; Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2; Negishi, E.; Coperet, C. Ma, S. Liou, S. Y.; Liu, F. Chem. Revs., 1996, 365; Mallern, J. L.; Fiaud, J. C.; Legros, J. Y. Hand book of Palladium- Catalyzed Organic Reactions, Academic Press, London, 1997.
34. Heck, R. F. Org. React., 1982, 27, 345; in Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991; Tsuji, J. Palladium Reagents and Catalysts, Wiley and Sons, 1995; Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2; Negishi, E.; Coperet, C. Ma, S. Liou, S. Y.; Liu, F. Chem. Revs., 1996, 365; Mallern, J. L.; Fiaud, J. C.; Legros, J. Y. Hand book of Palladium- Catalyzed Organic Reactions, Academic Press, London, 1997.
35. Heck, R. F. Org. React., 1982, 27, 345; in Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991; Tsuji, J. Palladium Reagents and Catalysts, Wiley and Sons, 1995; Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2; Negishi, E.; Coperet, C. Ma, S. Liou, S. Y.; Liu, F. Chem. Revs., 1996, 365; Mallern, J. L.; Fiaud, J. C.; Legros, J. Y. Hand book of Palladium- Catalyzed Organic Reactions, Academic Press, London, 1997.
36. Zhang, Y.; Negishi, E.-i. J. Am. Chem. Soc., 1989, 111, 3454; Trost, B. M. Acc. Chem. Res., 1990, 23, 34; Grigg, R.; Sukintha-lingam, S.; Sridharan, V. Tetrahedron Letters, 1991, 32, 2545; Meyer, F. E.; Bradenburg, J.; Parsons, P. J.; De Meijere, A. J. Chem. Soc., Chem. Commun., 1992, 390; Brown, S.; Clarkson, S. Grigg, R.; Sridharan, V. Tetrahedron Letters, 1993, 34, 157; Ma, S.; Negishi, E.-i. J. Am. Chem. Soc., 1995, 117, 6345.
37. Zhang, Y.; Negishi, E.-i. J. Am. Chem. Soc., 1989, 111, 3454; Trost, B. M. Acc. Chem. Res., 1990, 23, 34; Grigg, R.; Sukintha-lingam, S.; Sridharan, V. Tetrahedron Letters, 1991, 32, 2545; Meyer, F. E.; Bradenburg, J.; Parsons, P. J.; De Meijere, A. J. Chem. Soc., Chem. Commun., 1992, 390; Brown, S.; Clarkson, S. Grigg, R.; Sridharan, V. Tetrahedron Letters, 1993, 34, 157; Ma, S.; Negishi, E.-i. J. Am. Chem. Soc., 1995, 117, 6345.
38. Zhang, Y.; Negishi, E.-i. J. Am. Chem. Soc., 1989, 111, 3454; Trost, B. M. Acc. Chem. Res., 1990, 23, 34; Grigg, R.; Sukintha-lingam, S.; Sridharan, V. Tetrahedron Letters, 1991, 32, 2545; Meyer, F. E.; Bradenburg, J.; Parsons, P. J.; De Meijere, A. J. Chem. Soc., Chem. Commun., 1992, 390; Brown, S.; Clarkson, S. Grigg, R.; Sridharan, V. Tetrahedron Letters, 1993, 34, 157; Ma, S.; Negishi, E.-i. J. Am. Chem. Soc., 1995, 117, 6345.
39. Zhang, Y.; Negishi, E.-i. J. Am. Chem. Soc., 1989, 111, 3454; Trost, B. M. Acc. Chem. Res., 1990, 23, 34; Grigg, R.; Sukintha-lingam, S.; Sridharan, V. Tetrahedron Letters, 1991, 32, 2545; Meyer, F. E.; Bradenburg, J.; Parsons, P. J.; De Meijere, A. J. Chem. Soc., Chem. Commun., 1992, 390; Brown, S.; Clarkson, S. Grigg, R.; Sridharan, V. Tetrahedron Letters, 1993, 34, 157; Ma, S.; Negishi, E.-i. J. Am. Chem. Soc., 1995, 117, 6345.
40. Zhang, Y.; Negishi, E.-i. J. Am. Chem. Soc., 1989, 111, 3454; Trost, B. M. Acc. Chem. Res., 1990, 23, 34; Grigg, R.; Sukintha-lingam, S.; Sridharan, V. Tetrahedron Letters, 1991, 32, 2545; Meyer, F. E.; Bradenburg, J.; Parsons, P. J.; De Meijere, A. J. Chem. Soc., Chem. Commun., 1992, 390; Brown, S.; Clarkson, S. Grigg, R.; Sridharan, V. Tetrahedron Letters, 1993, 34, 157; Ma, S.; Negishi, E.-i. J. Am. Chem. Soc., 1995, 117, 6345.
41. Zhang, Y.; Negishi, E.-i. J. Am. Chem. Soc., 1989, 111, 3454; Trost, B. M. Acc. Chem. Res., 1990, 23, 34; Grigg, R.; Sukintha-lingam, S.; Sridharan, V. Tetrahedron Letters, 1991, 32, 2545; Meyer, F. E.; Bradenburg, J.; Parsons, P. J.; De Meijere, A. J. Chem. Soc., Chem. Commun., 1992, 390; Brown, S.; Clarkson, S. Grigg, R.; Sridharan, V. Tetrahedron Letters, 1993, 34, 157; Ma, S.; Negishi, E.-i. J. Am. Chem. Soc., 1995, 117, 6345.
42. Hegedus, L. S. Angew. Chem., Int. Ed. Engl., 1988, 27, 1113; Anderson, P. G.; Backvall, J. E. J. Am. Chem. Soc., 1992, 114, 8696; Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc., 1995, 117, 7255; Larock, R. C.; Yum, E. K. Tetrahedron, 1996, 52, 2743.
43. Hegedus, L. S. Angew. Chem., Int. Ed. Engl., 1988, 27, 1113; Anderson, P. G.; Backvall, J. E. J. Am. Chem. Soc., 1992, 114, 8696; Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc., 1995, 117, 7255; Larock, R. C.; Yum, E. K. Tetrahedron, 1996, 52, 2743.
44. Hegedus, L. S. Angew. Chem., Int. Ed. Engl., 1988, 27, 1113; Anderson, P. G.; Backvall, J. E. J. Am. Chem. Soc., 1992, 114, 8696; Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc., 1995, 117, 7255; Larock, R. C.; Yum, E. K. Tetrahedron, 1996, 52, 2743.
45. Hegedus, L. S. Angew. Chem., Int. Ed. Engl., 1988, 27, 1113; Anderson, P. G.; Backvall, J. E. J. Am. Chem. Soc., 1992, 114, 8696; Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc., 1995, 117, 7255; Larock, R. C.; Yum, E. K. Tetrahedron, 1996, 52, 2743.
46. The acetylenic carbinols were synthesised by addition of acetylene to the appropriate carbonyl compounds: cf Jones, E. R. H. and McCombie, J. T. J. Chem. Soc., 1942, 733; Campbell, K. N.; Campbell, B. K.; Eby, L. T. J. Am. Chem. Soc., 1938, 60, 2882.
47. The acetylenic carbinols were synthesised by addition of acetylene to the appropriate carbonyl compounds: cf Jones, E. R. H. and McCombie, J. T. J. Chem. Soc., 1942, 733; Campbell, K. N.; Campbell, B. K.; Eby, L. T. J. Am. Chem. Soc., 1938, 60, 2882.
48. + with the triple bond.
49. -1.
50. Bailey, W. F.; Patricia, J. J; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem., 1985, 50, 1999; Bailey, W. F.; Ovaska, T. V. Tetrahedron Letters, 1990, 31, 627; Bailey, W. F.; Khanolkar, A. D.; Kavaskar, K. V. J. Am. Chem. Soc., 1992, 114, 8053.
51. Bailey, W. F.; Patricia, J. J; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem., 1985, 50, 1999; Bailey, W. F.; Ovaska, T. V. Tetrahedron Letters, 1990, 31, 627; Bailey, W. F.; Khanolkar, A. D.; Kavaskar, K. V. J. Am. Chem. Soc., 1992, 114, 8053.
52. Bailey, W. F.; Patricia, J. J; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem., 1985, 50, 1999; Bailey, W. F.; Ovaska, T. V. Tetrahedron Letters, 1990, 31, 627; Bailey, W. F.; Khanolkar, A. D.; Kavaskar, K. V. J. Am. Chem. Soc., 1992, 114, 8053.
53. Ingham, C. F.; Massy-Westropp, R. A.; Reynolds, G. D.; Thorpe, W. D. Aust. J. Chem. 1975, 28, 2499; Harris, R. L. N.; Huppatz, J. L. Aust. J. Chem. 1977, 30, 2225; Hori, K.; Takaishi, N. Bull. Chem. Soc. Jpn., 1988, 61, 1791.
54. Ingham, C. F.; Massy-Westropp, R. A.; Reynolds, G. D.; Thorpe, W. D. Aust. J. Chem. 1975, 28, 2499; Harris, R. L. N.; Huppatz, J. L. Aust. J. Chem. 1977, 30, 2225; Hori, K.; Takaishi, N. Bull. Chem. Soc. Jpn., 1988, 61, 1791.
55. Ingham, C. F.; Massy-Westropp, R. A.; Reynolds, G. D.; Thorpe, W. D. Aust. J. Chem. 1975, 28, 2499; Harris, R. L. N.; Huppatz, J. L. Aust. J. Chem. 1977, 30, 2225; Hori, K.; Takaishi, N. Bull. Chem. Soc. Jpn., 1988, 61, 1791.