Photochemical and Lewis‐acid‐catalyzed rearrangement of 1‐phenyl‐4‐methyl‐3,6‐dioxabicyclo[3.1.0]hexan‐2‐one into its tetronic acid isomer

Maria J. Caus; Hans Cerfontain; Juan F. Piniella

doi:https://doi.org/10.1002/recl.19831021205

Photochemical and Lewis‐acid‐catalyzed rearrangement of 1‐phenyl‐4‐methyl‐3,6‐dioxabicyclo[3.1.0]hexan‐2‐one into its tetronic acid isomer

Maria J. Caus, Hans Cerfontain, Juan F. Piniella

Department of Geology

Research output: Contribution to journal › Article › Research › peer-review

Abstract

The irradiation of 2 in acetonitrile or methanol with λ 254 nm yields the tetronic acid derivative 3. The (thermal) BF3‐catalyzed rearrangement of 2 yields the same tetronic acid derivative. The structure of the tetronic acid 3 has been determined by means of X‐ray analysis; it forms monoclinic crystals with cell constants a = 10.868, b = 8.320, c = 20.936 Å and β = 90.65°. The space group is P21/n; in the unit cell there are eight molecules which exhibit intermolecular hydrogen bonding. Copyright © 1983 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

Original language	English
Pages (from-to)	515-519
Journal	Recueil des Travaux Chimiques des Pays‐Bas
Volume	102
DOIs	https://doi.org/10.1002/recl.19831021205
Publication status	Published - 1 Jan 1983

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title = "Photochemical and Lewis‐acid‐catalyzed rearrangement of 1‐phenyl‐4‐methyl‐3,6‐dioxabicyclo[3.1.0]hexan‐2‐one into its tetronic acid isomer",

abstract = "The irradiation of 2 in acetonitrile or methanol with λ 254 nm yields the tetronic acid derivative 3. The (thermal) BF3‐catalyzed rearrangement of 2 yields the same tetronic acid derivative. The structure of the tetronic acid 3 has been determined by means of X‐ray analysis; it forms monoclinic crystals with cell constants a = 10.868, b = 8.320, c = 20.936 {\AA} and β = 90.65°. The space group is P21/n; in the unit cell there are eight molecules which exhibit intermolecular hydrogen bonding. Copyright {\textcopyright} 1983 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim",

author = "Caus, {Maria J.} and Hans Cerfontain and Piniella, {Juan F.}",

year = "1983",

month = jan,

day = "1",

doi = "https://doi.org/10.1002/recl.19831021205",

language = "English",

volume = "102",

pages = "515--519",

}

Photochemical and Lewis‐acid‐catalyzed rearrangement of 1‐phenyl‐4‐methyl‐3,6‐dioxabicyclo[3.1.0]hexan‐2‐one into its tetronic acid isomer. / Caus, Maria J.; Cerfontain, Hans; Piniella, Juan F.

In: Recueil des Travaux Chimiques des Pays‐Bas, Vol. 102, 01.01.1983, p. 515-519.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Photochemical and Lewis‐acid‐catalyzed rearrangement of 1‐phenyl‐4‐methyl‐3,6‐dioxabicyclo[3.1.0]hexan‐2‐one into its tetronic acid isomer

AU - Caus, Maria J.

AU - Cerfontain, Hans

AU - Piniella, Juan F.

PY - 1983/1/1

Y1 - 1983/1/1

N2 - The irradiation of 2 in acetonitrile or methanol with λ 254 nm yields the tetronic acid derivative 3. The (thermal) BF3‐catalyzed rearrangement of 2 yields the same tetronic acid derivative. The structure of the tetronic acid 3 has been determined by means of X‐ray analysis; it forms monoclinic crystals with cell constants a = 10.868, b = 8.320, c = 20.936 Å and β = 90.65°. The space group is P21/n; in the unit cell there are eight molecules which exhibit intermolecular hydrogen bonding. Copyright © 1983 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

AB - The irradiation of 2 in acetonitrile or methanol with λ 254 nm yields the tetronic acid derivative 3. The (thermal) BF3‐catalyzed rearrangement of 2 yields the same tetronic acid derivative. The structure of the tetronic acid 3 has been determined by means of X‐ray analysis; it forms monoclinic crystals with cell constants a = 10.868, b = 8.320, c = 20.936 Å and β = 90.65°. The space group is P21/n; in the unit cell there are eight molecules which exhibit intermolecular hydrogen bonding. Copyright © 1983 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

U2 - https://doi.org/10.1002/recl.19831021205

DO - https://doi.org/10.1002/recl.19831021205

M3 - Article

VL - 102

SP - 515

EP - 519

ER -

Photochemical and Lewis‐acid‐catalyzed rearrangement of 1‐phenyl‐4‐methyl‐3,6‐dioxabicyclo[3.1.0]hexan‐2‐one into its tetronic acid isomer

Abstract

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