Bifunctionalized allenes. Part IV. 1,2λ5-oxaphosphole-3-carboxylates and 3-phosphoryl-2(5H)-furanones from 2-phosphoryl-2,3-alkadienoates

Heterocyclic Communications

Volumn 8, Issue 4, 2002, Pages 349-354

  Christov, Valerij Ch ^a   Prodanov, Boris ^a  

^a SHUMEN UNIVERSITY   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

4 BROMO 3 (DIMETHOXYPHOSPHORYL) 1 OXASPIRO[4.5]DEC 3 EN 2 ONE; 4 BROMO 3 (DIMETHOXYPHOSPHORYL) 5,5 DIMETHYL 2(5H) FURANONE; 4 BROMO 3 (DIPHENYLPHOSPHORYL) 1 OXASPIRO[4.5]DEC 3 EN 2 ONE; 4 BROMO 5,5 DIMETHYL 3 (DIPHENYLPHOSPHORYL) 2(5H) FURANONE; ALKADIENE; ALLENE DERIVATIVE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ETHYL 4 BROMO 2 METHOXY 1 OXA 2 OXO 2LAMBDA 5 PHOSPHASPIRO[4,5]DEC 3 EN 3 CARBOXYLATE; ETHYL 4 BROMO 2 METHOXY 5,5 DIMETHYL 2 OXO 2,5 DIHYDRO 1,2LAMBDA 5 OXAPHOSPHOLE 3 CARBOXYLATE; FURANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CYCLIZATION; SYNTHESIS;

EID: 0036409416     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2002.8.4.349     Document Type: Article

References (42)

1. For reviews on the allenes, see: (a) S. Patai (Ed.), The Chemistry of Ketenes, Allenes and Related Compounds, John Wiley & Sons, New York, 1980; (b) S. R. Landor (Ed.), The Chemistry of the Allenes, Academic Press, London, 1982; (c) D. J. Pasto, Tetrahedron, 40, 2805 (1984); (d) H. F. Schuster and G. M. Coppola, Allenes in Organic Synthesis, John Wiley & Sons, New York, 1988; (e) R. Zimmer, Synthesis, 165 (1993).
2. For reviews on the allenes, see: (a) S. Patai (Ed.), The Chemistry of Ketenes, Allenes and Related Compounds, John Wiley & Sons, New York, 1980; (b) S. R. Landor (Ed.), The Chemistry of the Allenes, Academic Press, London, 1982; (c) D. J. Pasto, Tetrahedron, 40, 2805 (1984); (d) H. F. Schuster and G. M. Coppola, Allenes in Organic Synthesis, John Wiley & Sons, New York, 1988; (e) R. Zimmer, Synthesis, 165 (1993).
3. For reviews on the allenes, see: (a) S. Patai (Ed.), The Chemistry of Ketenes, Allenes and Related Compounds, John Wiley & Sons, New York, 1980; (b) S. R. Landor (Ed.), The Chemistry of the Allenes, Academic Press, London, 1982; (c) D. J. Pasto, Tetrahedron, 40, 2805 (1984); (d) H. F. Schuster and G. M. Coppola, Allenes in Organic Synthesis, John Wiley & Sons, New York, 1988; (e) R. Zimmer, Synthesis, 165 (1993).
4. For reviews on the allenes, see: (a) S. Patai (Ed.), The Chemistry of Ketenes, Allenes and Related Compounds, John Wiley & Sons, New York, 1980; (b) S. R. Landor (Ed.), The Chemistry of the Allenes, Academic Press, London, 1982; (c) D. J. Pasto, Tetrahedron, 40, 2805 (1984); (d) H. F. Schuster and G. M. Coppola, Allenes in Organic Synthesis, John Wiley & Sons, New York, 1988; (e) R. Zimmer, Synthesis, 165 (1993).
5. For reviews on the allenes, see: (a) S. Patai (Ed.), The Chemistry of Ketenes, Allenes and Related Compounds, John Wiley & Sons, New York, 1980; (b) S. R. Landor (Ed.), The Chemistry of the Allenes, Academic Press, London, 1982; (c) D. J. Pasto, Tetrahedron, 40, 2805 (1984); (d) H. F. Schuster and G. M. Coppola, Allenes in Organic Synthesis, John Wiley & Sons, New York, 1988; (e) R. Zimmer, Synthesis, 165 (1993).
6. For reviews on the electrophilic addition to allenes, see: (a) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1966, pp. 250; (b) M. C. Caserio in Selective Organic Transformations, B. S. Thyagarajan (Ed.), John Wiley & Sons, New York, 1970. pp. 239; (c) G. H. Schmid and D. G. Garratt in The Chemistry of Double Bonded Functional Groups, S. Patai (Ed.), Wiley-Interscience, New York, 1977, pp. 725; (d) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1982, pp. 317; (e) T. L. Jacobs in The Chemistry of the Allenes, S. R. Landor (Ed.), Academic press, New York, 1982, Vol. 2, pp. 417; (f) W. Smadja, Chem. Rev., 83, 263 (1983).
7. For reviews on the electrophilic addition to allenes, see: (a) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1966, pp. 250; (b) M. C. Caserio in Selective Organic Transformations, B. S. Thyagarajan (Ed.), John Wiley & Sons, New York, 1970. pp. 239; (c) G. H. Schmid and D. G. Garratt in The Chemistry of Double Bonded Functional Groups, S. Patai (Ed.), Wiley-Interscience, New York, 1977, pp. 725; (d) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1982, pp. 317; (e) T. L. Jacobs in The Chemistry of the Allenes, S. R. Landor (Ed.), Academic press, New York, 1982, Vol. 2, pp. 417; (f) W. Smadja, Chem. Rev., 83, 263 (1983).
8. For reviews on the electrophilic addition to allenes, see: (a) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1966, pp. 250; (b) M. C. Caserio in Selective Organic Transformations, B. S. Thyagarajan (Ed.), John Wiley & Sons, New York, 1970. pp. 239; (c) G. H. Schmid and D. G. Garratt in The Chemistry of Double Bonded Functional Groups, S. Patai (Ed.), Wiley-Interscience, New York, 1977, pp. 725; (d) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1982, pp. 317; (e) T. L. Jacobs in The Chemistry of the Allenes, S. R. Landor (Ed.), Academic press, New York, 1982, Vol. 2, pp. 417; (f) W. Smadja, Chem. Rev., 83, 263 (1983).
9. For reviews on the electrophilic addition to allenes, see: (a) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1966, pp. 250; (b) M. C. Caserio in Selective Organic Transformations, B. S. Thyagarajan (Ed.), John Wiley & Sons, New York, 1970. pp. 239; (c) G. H. Schmid and D. G. Garratt in The Chemistry of Double Bonded Functional Groups, S. Patai (Ed.), Wiley-Interscience, New York, 1977, pp. 725; (d) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1982, pp. 317; (e) T. L. Jacobs in The Chemistry of the Allenes, S. R. Landor (Ed.), Academic press, New York, 1982, Vol. 2, pp. 417; (f) W. Smadja, Chem. Rev., 83, 263 (1983).
10. For reviews on the electrophilic addition to allenes, see: (a) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1966, pp. 250; (b) M. C. Caserio in Selective Organic Transformations, B. S. Thyagarajan (Ed.), John Wiley & Sons, New York, 1970. pp. 239; (c) G. H. Schmid and D. G. Garratt in The Chemistry of Double Bonded Functional Groups, S. Patai (Ed.), Wiley-Interscience, New York, 1977, pp. 725; (d) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1982, pp. 317; (e) T. L. Jacobs in The Chemistry of the Allenes, S. R. Landor (Ed.), Academic press, New York, 1982, Vol. 2, pp. 417; (f) W. Smadja, Chem. Rev., 83, 263 (1983).
11. For reviews on the electrophilic addition to allenes, see: (a) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1966, pp. 250; (b) M. C. Caserio in Selective Organic Transformations, B. S. Thyagarajan (Ed.), John Wiley & Sons, New York, 1970. pp. 239; (c) G. H. Schmid and D. G. Garratt in The Chemistry of Double Bonded Functional Groups, S. Patai (Ed.), Wiley-Interscience, New York, 1977, pp. 725; (d) P. B. D. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevior, Amsterdam, 1982, pp. 317; (e) T. L. Jacobs in The Chemistry of the Allenes, S. R. Landor (Ed.), Academic press, New York, 1982, Vol. 2, pp. 417; (f) W. Smadja, Chem. Rev., 83, 263 (1983).
12. For electrophile-induced heterocyclizations of monofunctionalized allenes, see: (a) T. L. Jacobs, R. Macomber and D. Zucker, J. Am. Chem. Soc., 89, 7001 (1967); (b) F. Toda, T. Komora and K. Akagi, Bull. Chem. Soc. Jpn., 41, 1493 (1968); (c) S. Hoft and L. Brandsma, Rec. Trav. Chim. Pays-Bas, 88, 845 (1969); (d) R. Gelin, S. Gelin and M. Albrand, Bull. Soc. Chim. Fr., 720 (1972); (e) L. I. Olsson and A. Claesson, Synthesis, 743 (1979); (f) P. L. Beaulieu, V. M. Morisset and D. G. Garratt, Tetrahedron Lett., 21, 129 (1980).
13. For electrophile-induced heterocyclizations of monofunctionalized allenes, see: (a) T. L. Jacobs, R. Macomber and D. Zucker, J. Am. Chem. Soc., 89, 7001 (1967); (b) F. Toda, T. Komora and K. Akagi, Bull. Chem. Soc. Jpn., 41, 1493 (1968); (c) S. Hoft and L. Brandsma, Rec. Trav. Chim. Pays-Bas, 88, 845 (1969); (d) R. Gelin, S. Gelin and M. Albrand, Bull. Soc. Chim. Fr., 720 (1972); (e) L. I. Olsson and A. Claesson, Synthesis, 743 (1979); (f) P. L. Beaulieu, V. M. Morisset and D. G. Garratt, Tetrahedron Lett., 21, 129 (1980).
14. For electrophile-induced heterocyclizations of monofunctionalized allenes, see: (a) T. L. Jacobs, R. Macomber and D. Zucker, J. Am. Chem. Soc., 89, 7001 (1967); (b) F. Toda, T. Komora and K. Akagi, Bull. Chem. Soc. Jpn., 41, 1493 (1968); (c) S. Hoft and L. Brandsma, Rec. Trav. Chim. Pays-Bas, 88, 845 (1969); (d) R. Gelin, S. Gelin and M. Albrand, Bull. Soc. Chim. Fr., 720 (1972); (e) L. I. Olsson and A. Claesson, Synthesis, 743 (1979); (f) P. L. Beaulieu, V. M. Morisset and D. G. Garratt, Tetrahedron Lett., 21, 129 (1980).
15. For electrophile-induced heterocyclizations of monofunctionalized allenes, see: (a) T. L. Jacobs, R. Macomber and D. Zucker, J. Am. Chem. Soc., 89, 7001 (1967); (b) F. Toda, T. Komora and K. Akagi, Bull. Chem. Soc. Jpn., 41, 1493 (1968); (c) S. Hoft and L. Brandsma, Rec. Trav. Chim. Pays-Bas, 88, 845 (1969); (d) R. Gelin, S. Gelin and M. Albrand, Bull. Soc. Chim. Fr., 720 (1972); (e) L. I. Olsson and A. Claesson, Synthesis, 743 (1979); (f) P. L. Beaulieu, V. M. Morisset and D. G. Garratt, Tetrahedron Lett., 21, 129 (1980).
16. For electrophile-induced heterocyclizations of monofunctionalized allenes, see: (a) T. L. Jacobs, R. Macomber and D. Zucker, J. Am. Chem. Soc., 89, 7001 (1967); (b) F. Toda, T. Komora and K. Akagi, Bull. Chem. Soc. Jpn., 41, 1493 (1968); (c) S. Hoft and L. Brandsma, Rec. Trav. Chim. Pays-Bas, 88, 845 (1969); (d) R. Gelin, S. Gelin and M. Albrand, Bull. Soc. Chim. Fr., 720 (1972); (e) L. I. Olsson and A. Claesson, Synthesis, 743 (1979); (f) P. L. Beaulieu, V. M. Morisset and D. G. Garratt, Tetrahedron Lett., 21, 129 (1980).
17. For electrophile-induced heterocyclizations of monofunctionalized allenes, see: (a) T. L. Jacobs, R. Macomber and D. Zucker, J. Am. Chem. Soc., 89, 7001 (1967); (b) F. Toda, T. Komora and K. Akagi, Bull. Chem. Soc. Jpn., 41, 1493 (1968); (c) S. Hoft and L. Brandsma, Rec. Trav. Chim. Pays-Bas, 88, 845 (1969); (d) R. Gelin, S. Gelin and M. Albrand, Bull. Soc. Chim. Fr., 720 (1972); (e) L. I. Olsson and A. Claesson, Synthesis, 743 (1979); (f) P. L. Beaulieu, V. M. Morisset and D. G. Garratt, Tetrahedron Lett., 21, 129 (1980).
18. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
19. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
20. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
21. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
22. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
23. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
24. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
25. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
26. For electrophile-induced heterocyclizations of allenecarboxylic acids and esters, see: (a) E. P. Kohler and W. J. Whicher, J. Am. Chem. Soc., 62, 1489 (1940); (b) G. Aksnes and P. Froeyen, Acta Chim Scand., 22, 2347 (1968); (c) K. Shingu, S. Hagishita and M. Nakagawa, Tetrahedron Lett., 4371 (1967); (d) G. Kresze, W. Runge and E. Ruch, Liebigs Ann. Chem., 756, 112 (1972); (e) S. Musierowicz, A. E. Wroblewski and H. Krawczyk, Tetrahedron Lett., 1437 (1975); (f) G. Kresze, W. L. Kloimstein and W. Runge, Liebigs Ann. Chem., 760, 979 (1976); (g) S. Musierowicz and A. E. Wroblewski, Tetrahedron, 34, 461 (1978); (h) G. B. Gill and M. S. H. Idris, Tetrahedron Lett., 26, 4811 (1985); (i) J. A. Marshal and E. M. Wallace, J. Org. Chem., 60, 796 (1995).
27. For electrophile-induced heterocyclizations of sulfur containing allenes, see: (a) L. Horner and V. Binder, Liebigs Ann. Chem., 757, 33 (1972); (b) S. Braverman and D. Reisman, Tetrahedron Lett., 1753 (1977); (c) S. Braverman and D. Reisman, J. Am. Chem. Soc., 99, 605 (1977); (d) S. Braverman and Y. Duar, J. Am. Chem. Soc., 105, 1061 (1983).
28. For electrophile-induced heterocyclizations of sulfur containing allenes, see: (a) L. Horner and V. Binder, Liebigs Ann. Chem., 757, 33 (1972); (b) S. Braverman and D. Reisman, Tetrahedron Lett., 1753 (1977); (c) S. Braverman and D. Reisman, J. Am. Chem. Soc., 99, 605 (1977); (d) S. Braverman and Y. Duar, J. Am. Chem. Soc., 105, 1061 (1983).
29. For electrophile-induced heterocyclizations of sulfur containing allenes, see: (a) L. Horner and V. Binder, Liebigs Ann. Chem., 757, 33 (1972); (b) S. Braverman and D. Reisman, Tetrahedron Lett., 1753 (1977); (c) S. Braverman and D. Reisman, J. Am. Chem. Soc., 99, 605 (1977); (d) S. Braverman and Y. Duar, J. Am. Chem. Soc., 105, 1061 (1983).
30. For electrophile-induced heterocyclizations of sulfur containing allenes, see: (a) L. Horner and V. Binder, Liebigs Ann. Chem., 757, 33 (1972); (b) S. Braverman and D. Reisman, Tetrahedron Lett., 1753 (1977); (c) S. Braverman and D. Reisman, J. Am. Chem. Soc., 99, 605 (1977); (d) S. Braverman and Y. Duar, J. Am. Chem. Soc., 105, 1061 (1983).
31. For reviews on the heterocyclization of phosphorylated allenes in the reaction with electrophilic reagents, see: (a) Ch. M. Angelov, Phosphorus and Sulfur, 15, 177 (1983); (b) N G. Khusainova and A. N. Pudovik, Usp. Khim., 56, 975 (1987); (c) I. V. Alabugin and V. K. Brel, Russ. Chem. Rev., 66, 205 (1997).
32. For reviews on the heterocyclization of phosphorylated allenes in the reaction with electrophilic reagents, see: (a) Ch. M. Angelov, Phosphorus and Sulfur, 15, 177 (1983); (b) N G. Khusainova and A. N. Pudovik, Usp. Khim., 56, 975 (1987); (c) I. V. Alabugin and V. K. Brel, Russ. Chem. Rev., 66, 205 (1997).
33. For reviews on the heterocyclization of phosphorylated allenes in the reaction with electrophilic reagents, see: (a) Ch. M. Angelov, Phosphorus and Sulfur, 15, 177 (1983); (b) N G. Khusainova and A. N. Pudovik, Usp. Khim., 56, 975 (1987); (c) I. V. Alabugin and V. K. Brel, Russ. Chem. Rev., 66, 205 (1997).
34. Previous reports on bifunctionalized allenes, see: (a) Part. I. V. Ch. Christov and B. Prodanov, Phosphorus, Sulfur, Silicon, 166, 265 (2000); (b) Part. II. V. Ch. Christov, B. Prodanov and R. Nikolova, Phosphorus, Sulfur, Silicon, 166, 275 (2000); (c) Part. III. V. Ch. Christov and B. Prodanov, Phosphorus, Sulfur, Silicon, 177, (2001).
35. Previous reports on bifunctionalized allenes, see: (a) Part. I. V. Ch. Christov and B. Prodanov, Phosphorus, Sulfur, Silicon, 166, 265 (2000); (b) Part. II. V. Ch. Christov, B. Prodanov and R. Nikolova, Phosphorus, Sulfur, Silicon, 166, 275 (2000); (c) Part. III. V. Ch. Christov and B. Prodanov, Phosphorus, Sulfur, Silicon, 177, (2001).
36. Previous reports on bifunctionalized allenes, see: (a) Part. I. V. Ch. Christov and B. Prodanov, Phosphorus, Sulfur, Silicon, 166, 265 (2000); (b) Part. II. V. Ch. Christov, B. Prodanov and R. Nikolova, Phosphorus, Sulfur, Silicon, 166, 275 (2000); (c) Part. III. V. Ch. Christov and B. Prodanov, Phosphorus, Sulfur, Silicon, 177, (2001).
37. For synthesis of phosphonium salts by electrophile-induced heterocyclizations of allenyl phosphine oxides, see: (a) Ch. M. Angelov, Ch. Zh. Christov and B. I. Ionin, Zh. Obshch. Khim., 52, 264 (1982); Chem. Abstr.: 96, 181360t (1982); (b) N. G. Khusainova, L. V. Naumova, E. A. Berdnikov and A. N. Pudovik, Zh. Obshch. Khim., 52, 1040 (1982); Chem. Abstr.: 97, 1110109c (1982); (c) Ch. M. Angelov and D. D. Enchev, Phosphorus and Sulfur, 37, 125 (1988); (d) D. D. Enchev, Ch. M. Angelov, E. Krawchik, A. Skowronska and J. Michalski, Phosphorus and Sulfur, 57, 249 (1991).
38. For synthesis of phosphonium salts by electrophile-induced heterocyclizations of allenyl phosphine oxides, see: (a) Ch. M. Angelov, Ch. Zh. Christov and B. I. Ionin, Zh. Obshch. Khim., 52, 264 (1982); Chem. Abstr.: 96, 181360t (1982); (b) N. G. Khusainova, L. V. Naumova, E. A. Berdnikov and A. N. Pudovik, Zh. Obshch. Khim., 52, 1040 (1982); Chem. Abstr.: 97, 1110109c (1982); (c) Ch. M. Angelov and D. D. Enchev, Phosphorus and Sulfur, 37, 125 (1988); (d) D. D. Enchev, Ch. M. Angelov, E. Krawchik, A. Skowronska and J. Michalski, Phosphorus and Sulfur, 57, 249 (1991).
39. For synthesis of phosphonium salts by electrophile-induced heterocyclizations of allenyl phosphine oxides, see: (a) Ch. M. Angelov, Ch. Zh. Christov and B. I. Ionin, Zh. Obshch. Khim., 52, 264 (1982); Chem. Abstr.: 96, 181360t (1982); (b) N. G. Khusainova, L. V. Naumova, E. A. Berdnikov and A. N. Pudovik, Zh. Obshch. Khim., 52, 1040 (1982); Chem. Abstr.: 97, 1110109c (1982); (c) Ch. M. Angelov and D. D. Enchev, Phosphorus and Sulfur, 37, 125 (1988); (d) D. D. Enchev, Ch. M. Angelov, E. Krawchik, A. Skowronska and J. Michalski, Phosphorus and Sulfur, 57, 249 (1991).
40. For synthesis of phosphonium salts by electrophile-induced heterocyclizations of allenyl phosphine oxides, see: (a) Ch. M. Angelov, Ch. Zh. Christov and B. I. Ionin, Zh. Obshch. Khim., 52, 264 (1982); Chem. Abstr.: 96, 181360t (1982); (b) N. G. Khusainova, L. V. Naumova, E. A. Berdnikov and A. N. Pudovik, Zh. Obshch. Khim., 52, 1040 (1982); Chem. Abstr.: 97, 1110109c (1982); (c) Ch. M. Angelov and D. D. Enchev, Phosphorus and Sulfur, 37, 125 (1988); (d) D. D. Enchev, Ch. M. Angelov, E. Krawchik, A. Skowronska and J. Michalski, Phosphorus and Sulfur, 57, 249 (1991).
41. For synthesis of phosphonium salts by electrophile-induced heterocyclizations of allenyl phosphine oxides, see: (a) Ch. M. Angelov, Ch. Zh. Christov and B. I. Ionin, Zh. Obshch. Khim., 52, 264 (1982); Chem. Abstr.: 96, 181360t (1982); (b) N. G. Khusainova, L. V. Naumova, E. A. Berdnikov and A. N. Pudovik, Zh. Obshch. Khim., 52, 1040 (1982); Chem. Abstr.: 97, 1110109c (1982); (c) Ch. M. Angelov and D. D. Enchev, Phosphorus and Sulfur, 37, 125 (1988); (d) D. D. Enchev, Ch. M. Angelov, E. Krawchik, A. Skowronska and J. Michalski, Phosphorus and Sulfur, 57, 249 (1991).
42. For synthesis of phosphonium salts by electrophile-induced heterocyclizations of allenyl phosphine oxides, see: (a) Ch. M. Angelov, Ch. Zh. Christov and B. I. Ionin, Zh. Obshch. Khim., 52, 264 (1982); Chem. Abstr.: 96, 181360t (1982); (b) N. G. Khusainova, L. V. Naumova, E. A. Berdnikov and A. N. Pudovik, Zh. Obshch. Khim., 52, 1040 (1982); Chem. Abstr.: 97, 1110109c (1982); (c) Ch. M. Angelov and D. D. Enchev, Phosphorus and Sulfur, 37, 125 (1988); (d) D. D. Enchev, Ch. M. Angelov, E. Krawchik, A. Skowronska and J. Michalski, Phosphorus and Sulfur, 57, 249 (1991).