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Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with (R)-phenylglycinol

Vadim A Soloshonok 1
Vadim A Soloshonok
, 
Hironari Ohkura 1
Hironari Ohkura
, 
Manabu Yasumoto 1
Manabu Yasumoto
10.1070/MC2006v016n03ABEH002298
Published 2006-07-06
Communication , Volume 16, Issue 3, 165-167
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Soloshonok V. A., Ohkura H., Yasumoto M. Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with (R)-phenylglycinol // Mendeleev Communications. 2006. Vol. 16. No. 3. pp. 165-167.
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Soloshonok V. A., Ohkura H., Yasumoto M. Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with (R)-phenylglycinol // Mendeleev Communications. 2006. Vol. 16. No. 3. pp. 165-167.
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TY - JOUR
DO - 10.1070/MC2006v016n03ABEH002298
UR - https://mendcomm.colab.ws/publications/10.1070/MC2006v016n03ABEH002298
TI - Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with (R)-phenylglycinol
T2 - Mendeleev Communications
AU - Soloshonok, Vadim A
AU - Ohkura, Hironari
AU - Yasumoto, Manabu
PY - 2006
DA - 2006/07/06
PB - Mendeleev Communications
SP - 165-167
IS - 3
VL - 16
ER -
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@article{2006_Soloshonok,
author = {Vadim A Soloshonok and Hironari Ohkura and Manabu Yasumoto},
title = {Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with (R)-phenylglycinol},
journal = {Mendeleev Communications},
year = {2006},
volume = {16},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2006v016n03ABEH002298},
number = {3},
pages = {165--167},
doi = {10.1070/MC2006v016n03ABEH002298}
}
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Soloshonok, Vadim A., et al. “Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with (R)-phenylglycinol.” Mendeleev Communications, vol. 16, no. 3, Jul. 2006, pp. 165-167. https://mendcomm.colab.ws/publications/10.1070/MC2006v016n03ABEH002298.

Abstract

The reaction of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with (R)-phenylglycinol proceeds via the intermediate formation of (R,4E,6Z)-5,7-bis(trifluoromethyl)-2,3-dihydro-3-phenyl-1,4-oxazepine, which further undergoes a base-catalysed 1,3-proton shift followed by [1,2] Wittig rearrangement giving rise to 2,4-bis(trifluoromethyl)-6-phenylpyridine.

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