Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement

Angewandte Chemie - International Edition

Volumn 42, Issue 21, 2003, Pages 2389-2392

  Renard, Pierre Yves ^a   Vayron, Philippe ^a   Leclerc, Eric ^a   Valleix, Alain ^a   Mioskowski, Charles ^b  

^a CEA SACLAY   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Lewis acids; Michaelis Arbuzov rearrangement; Phosphorus; Rearrangement

Indexed keywords

CATALYSIS; PHOSPHORUS COMPOUNDS; THERMAL EFFECTS;

LEWIS ACID;

ORGANIC ACIDS;

LEWIS ACID; PHOSPHITE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYLSILYL DERIVATIVE;

ARBUZOV REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 0038343586     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250270     Document Type: Article

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17. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
18. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
19. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
20. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
21. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
22. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
23. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
24. a) T. Janecki R. Bodalski, Synthesis 1990, 799-801; b) R. S. Macomber, D. E. Rardon, D. M. Ho, J. Org. Chem. 1992, 57, 3874-3881; c) S. Demay, K. Harms, P. Knochel, Tetrahedron Lett. 1999, 40, 4981-4984; d) W. G. Bentrude, S. G. Lee, K. Akutagawa, W. Ye, Y. Charbonnel, J. Am. Chem. Soc. 1987, 109, 1577; e) D. Shukla, C. Lu, N. P. Schepp, W. G. Bentrude, L. J. Johnston, J. Org. Chem. 2000, 65, 6167-6172; f) T. Wada, Y. Sato, F. Honda, S.-I. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997 119, 12710-12721; g) M. R. Banks, R. F. Hudson, J. Chem. Soc. Perkin Trans. 2 1989, 463-467; h) A. E. Arbuzov, K. V. Nikonorov, Zh. Obshch. Khim. 1948, 18, 2008; h) V. Mark, Mech. Mol. Migr. 1969, 2, 319-437. Noteworthy is the spontaneous rearrangement of particularly activated triarylmethyl phosphorus-3-esters, for instance D.V.D. Hardy, H. H. Hatt, J. Chem. Soc. 1952, 3778-3783, and references therein.
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