Vinylphosphonium Salts and Allenes from Carbonyl Compounds Using Titanium-Substituted Ylides

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2564-2573

  Reynolds, Kelly A ^a   Dopico, Pablo G ^a   Brody, Marcus S ^a   Finn, M G ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001641853     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961000d     Document Type: Article

References (82)

1. Reynolds, K. A.; Dopico, P. G.; Sundermann, M. J.; Hughes, K. A.; Finn, M. G. J. Org. Chem. 1993, 58, 1298-1299.
2. Another "triply convergent" allene synthesis has been developed, comprising a three-step procedure involving thermal decarboxylation of α-alklyidene-β-lactones: Danheiser, R. L.; Choi, Y. M.; Menichincheri, M.; Stoner, E. J. J. Org. Chem. 1993, 58, 322-327.
3. The majority of allene syntheses involve the rearrangement of bonds in an existing three-carbon skeleton [see reference 5a,b]. Common examples include the dehydrohalogenation or reductive elimination of vinylic halides, and addition/elimination reactions of acetylenes (Pasto, D. J.; Shults, R. H.; McGrath, J. A.; Waterhouse, A. J. Org. Chem. 1978, 43, 1382-1384. Pasto, D. J.; Chou, S.-K.; Waterhouse, A.; Shults, R. H.; Hennion, G. F. J. Org. Chem. 1978, 43, 1385-1388. Pasto, D. J.; Chou, S.-K.; Fritzer, E.; Shults, W.; Hennion, G. F. J. Org. Chem. 1978, 43, 1389-1394). Other methods include elimination of silyl groups (Chan, T. H.; Mychajlowskij, W. Tetrahedron Lett. 1974, 171-174) and reductive eliminations of halogenated cyclopropanes (Binger, P. Synthesis 1974, 190-192).
4. The majority of allene syntheses involve the rearrangement of bonds in an existing three-carbon skeleton [see reference 5a,b]. Common examples include the dehydrohalogenation or reductive elimination of vinylic halides, and addition/elimination reactions of acetylenes (Pasto, D. J.; Shults, R. H.; McGrath, J. A.; Waterhouse, A. J. Org. Chem. 1978, 43, 1382-1384. Pasto, D. J.; Chou, S.-K.; Waterhouse, A.; Shults, R. H.; Hennion, G. F. J. Org. Chem. 1978, 43, 1385-1388. Pasto, D. J.; Chou, S.-K.; Fritzer, E.; Shults, W.; Hennion, G. F. J. Org. Chem. 1978, 43, 1389-1394). Other methods include elimination of silyl groups (Chan, T. H.; Mychajlowskij, W. Tetrahedron Lett. 1974, 171-174) and reductive eliminations of halogenated cyclopropanes (Binger, P. Synthesis 1974, 190-192).
5. The majority of allene syntheses involve the rearrangement of bonds in an existing three-carbon skeleton [see reference 5a,b]. Common examples include the dehydrohalogenation or reductive elimination of vinylic halides, and addition/elimination reactions of acetylenes (Pasto, D. J.; Shults, R. H.; McGrath, J. A.; Waterhouse, A. J. Org. Chem. 1978, 43, 1382-1384. Pasto, D. J.; Chou, S.-K.; Waterhouse, A.; Shults, R. H.; Hennion, G. F. J. Org. Chem. 1978, 43, 1385-1388. Pasto, D. J.; Chou, S.-K.; Fritzer, E.; Shults, W.; Hennion, G. F. J. Org. Chem. 1978, 43, 1389-1394). Other methods include elimination of silyl groups (Chan, T. H.; Mychajlowskij, W. Tetrahedron Lett. 1974, 171-174) and reductive eliminations of halogenated cyclopropanes (Binger, P. Synthesis 1974, 190-192).
6. The majority of allene syntheses involve the rearrangement of bonds in an existing three-carbon skeleton [see reference 5a,b]. Common examples include the dehydrohalogenation or reductive elimination of vinylic halides, and addition/elimination reactions of acetylenes (Pasto, D. J.; Shults, R. H.; McGrath, J. A.; Waterhouse, A. J. Org. Chem. 1978, 43, 1382-1384. Pasto, D. J.; Chou, S.-K.; Waterhouse, A.; Shults, R. H.; Hennion, G. F. J. Org. Chem. 1978, 43, 1385-1388. Pasto, D. J.; Chou, S.-K.; Fritzer, E.; Shults, W.; Hennion, G. F. J. Org. Chem. 1978, 43, 1389-1394). Other methods include elimination of silyl groups (Chan, T. H.; Mychajlowskij, W. Tetrahedron Lett. 1974, 171-174) and reductive eliminations of halogenated cyclopropanes (Binger, P. Synthesis 1974, 190-192).
7. The majority of allene syntheses involve the rearrangement of bonds in an existing three-carbon skeleton [see reference 5a,b]. Common examples include the dehydrohalogenation or reductive elimination of vinylic halides, and addition/elimination reactions of acetylenes (Pasto, D. J.; Shults, R. H.; McGrath, J. A.; Waterhouse, A. J. Org. Chem. 1978, 43, 1382-1384. Pasto, D. J.; Chou, S.-K.; Waterhouse, A.; Shults, R. H.; Hennion, G. F. J. Org. Chem. 1978, 43, 1385-1388. Pasto, D. J.; Chou, S.-K.; Fritzer, E.; Shults, W.; Hennion, G. F. J. Org. Chem. 1978, 43, 1389-1394). Other methods include elimination of silyl groups (Chan, T. H.; Mychajlowskij, W. Tetrahedron Lett. 1974, 171-174) and reductive eliminations of halogenated cyclopropanes (Binger, P. Synthesis 1974, 190-192).
8. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
9. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
10. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
11. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
12. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
13. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
14. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
15. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
16. 2 with a tantalum alkylidene complex: Schrock, R. R. J. Am. Chem. Soc. 1976, 98, 5399-5400. (f) Olefination of a ketene: Meyer, J.; Wittig, G.; Scholkopf, U. Chem. Ber. 1956, 89, 842. (g) Using an intermediate titanium vinylidene: Buchwald, S. L.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 105, 5490-5491. (h) The combination of Peterson- and Wittig-type olefination processes for the synthesis of allenes was suggested in: Chan, T. H.; Chang, E. J. Org. Chem. 1974, 39, 3264-3268. Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 230-236.
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44. iPr are discussed in the accompanying paper.
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49. Reynolds, K. A.; Finn, M. G., subsequent paper in this issue.
50. 1
51. Phosphonium compounds 4 and 3y were separated on a short silica gel chromatography column.
52. PC 175 Hz. See also the subsequent paper in this issue.
53. PC 175 Hz. See also the subsequent paper in this issue.
54. Similar resonance forms have been invoked to explain NMR chemical shifts in vinylphosphonium salts: reference 10, and Albright, T. A.; Freeman, W. J.; Schweizer, E. E. J. Am. Chem. Soc. 1975, 97, 2946-2950.
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69. 26 is used. See Experimental Section.
70. Reactions performed with 1 equiv of PhLi show a marked increase in allene yield as the vinylphosphonium and PhLi are allowed to react for longer periods prior to addition of the trapping aldehyde, reaching a maximum of 70% upon addition of 1 equiv of PhLi at -78 °C for 3.5 h, or at -42°C for 15 min. Only a trace of allene is formed from a reaction at 0°C for 3 min.
71. Derived from Benson, S. W. Thermochemical Kinetics; John Wiley & Sons: New York, 1976; see tables on pp 273-4.
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79. Dopico, P. G. Ph.D. Thesis, University of Virginia, 1995.
80. McGrath, D. Ph.D. Thesis, California Institute of Technology, 1992. We thank Prof. McGrath for bringing this method to our attention.
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