Bildung von 1,2-Dioxolanen aus Cyclopropanen

Formation of 1,2-Dioxolanes from Cyclopropanes The already known carenols 5 and 7 are obtained by stereoselective oxirane cleavage of (1S,3S,4R,6R)-( + )-3α,4α-epoxycarane (4). Autoxidation of the ketone 8, derived from 7, failed to give any 1,2-dioxolane derivatives. 5 is converted to the hydroperoxide 9 by cyclopropane opening using 70% hydrogen peroxide solution. Cyclization of 9 with lead tetraacetate affords the dioxolane 10.

[1]  D. Wiemer,et al.  Synthesis and reactions of (-)- and (+)-carenones , 1984 .

[2]  M. Chmielewski,et al.  The conformation of t-butyl 2-methoxy-5, 6-dihydro-2 H-pyran-6-carboxylates and 6,6′- disubstituted 2-methoxy-5,6-dihydro-2H-pyran derivatives on the basis of 1H and 13 C NMR spectra† , 1982 .

[3]  N. Porter,et al.  Serial Cyclization of an Arachidonic Acid Hydroperoxide , 1982 .

[4]  G. Rücker,et al.  Zur Konfiguration des Nardosinons , 1981 .

[5]  Bruce A. Weber,et al.  Unified mechanism for polyunsaturated fatty acid autoxidation. Competition of peroxy radical hydrogen atom abstraction, .beta.-scission, and cyclization , 1981 .

[6]  H. Takeshita,et al.  Synthetic Photochemistry. XXL. The Sensitized Photooxygenation of Calarene. A Facile Hock Cleavage of an Allylhydroperoxide and Structure Revision for Aristolenols , 1980 .

[7]  A. Meijere Bonding Properties of Cyclopropane and Their Chemical Consequences , 1979 .

[8]  A. D. Meijere Bindungseigenschaften des Cyclopropans und chemische Konsequenzen , 1979 .

[9]  D. Ginsburg,et al.  Reaction of bicyclic dienes with 4-substituted-1,2,4-triazoline-3,5-diones , 1977 .

[10]  Roy A. Johnson,et al.  Superoxide chemistry. Convenient synthesis of dialkyl peroxides , 1975 .

[11]  E. Kleinpeter,et al.  1H‐NMR‐Spektroskopische Untersuchungen an methylsubstituierten Cyclohexen‐(4)‐dicarbonsäure‐(1,2)‐anhydriden , 1973 .

[12]  W. Huber,et al.  Ein neues Sprühreagens zum Nachweis und zur quantitativen Bestimmung von Peroxiden , 1972 .

[13]  G. Rücker Zur Struktur des Nardosinons, III. Ableitung einer Konstitutionsformel für das Nardosinon und Struktur der Hydrierungsprodukte , 1969 .

[14]  K. Gollnick,et al.  Absolute Konfigurationen von Verbindungen der Caran‐ und m‐Menthan‐Reihe1) , 1969 .

[15]  H. Brown,et al.  Hydroboration of Terpenes. IV. Hydroboration of (+)-3-Carene ([UNK]3-Carene). Configuration Assignments for the 4-Caranols and 4-Caranones. An Unusual Stability of 4-Isocaranone with a cis Relationship of the Methyl and gem-Dimethyl Groups , 1967 .

[16]  K. Gollnick,et al.  Studien in der caranreihe—IV : Über die umlagerung von (-) (ir:4s:6s)-Δ2-caren-trans-4-ol in (-) (5s)-1-methyl-5-(α-hydroxyisopropyl)-cyclohexa-1,3-dien , 1966 .

[17]  G. Ohloff,et al.  Zur photosensibilisierten O2‐Übertragung auf (+)‐Caren‐(3) , 1965 .

[18]  E. W. Garbisch Conformations. VI. Vinyl-Allylic Proton Spin Couplings , 1964 .