Carbon‐13 NMR analysis of cyclobutane dimers from benzocycloalkenes

Browne, Clinton E.; Ruehle, P. H.; Dobbs, T. K.; Eisenbraun, E. J.

doi:10.1002/mrc.1270121002

Cited by 6 publications

(1 citation statement)

References 14 publications

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“…The Wharron rearrangement of a diastereoisomeric mixture of epoxides derived from 9 has already been described by Stothers el al. [8], but only the cis-isomer 10 had been fully characterized. See also [9].…”

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confidence: 99%

1,2,3,4,4a,5,8,8a‐Octahydro‐4β,8aα‐dimethylnaphthalen‐4aβ‐ol ( = Dehydrogeosmin), a Novel Compound Occurring in the Flower Scent of Various Species of cactaceae

Kaiser¹,

Nussbaumer²

1990

Helvetica Chimica Acta

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The 1,2,3,4,4a,5,8,8a-octahydro-4b,8aa -dimethylnaphthalen-4aB-ol( = dehydrogeosmin; 1) has been identitied as the olfactorily dominant compound in the flower Scents of Rebutia marsoneri WERD., Dolichothele longimummu (DC.) BR. et R., and Sulcorebutiu kruegeri (CARD.) RITT. The structure of 1, which might be of importance to the pollination biology of such Cactaceue, is based on spectral data and synthesis.

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confidence: 99%

1,2,3,4,4a,5,8,8a‐Octahydro‐4β,8aα‐dimethylnaphthalen‐4aβ‐ol ( = Dehydrogeosmin), a Novel Compound Occurring in the Flower Scent of Various Species of cactaceae

Kaiser¹,

Nussbaumer²

1990

Helvetica Chimica Acta

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NMR Spectroscopy of Cyclobutanes

Seidl

Dias

2009

Patai's Chemistry of Functional Groups

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Conformations and ¹³C NMR shifts in tetralins

Schneider

Agrawal

1984

Org. Magn. Reson.

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TETRALINS: STRUCTURESHIELDING RELATIONSHIPSThe conformational and spectroscopic analysis of the tetralin skeleton is of relevance for many natural products, e.g. for several sesquiterpenoids, lignan or chroman derivatives. Further, tetralins show a wide spectrum of biological activity?3 which only can be understood on the basis of a detailed knowledge of their molecular structure. The presence of a flexible non-chair cyclohexene ring in these compounds (Scheme 1) provides a particular challenge for the use of 13C NMR shifts for configurational and conformational assignments.Crystallographic structure determinations have been carried out for several tetralin derivative^;^ in view of the vicinal halogen substituents present in these compounds, however, it is difficult to infer the conformation of the basic skeleton from these measurements. Molecular mechanics calculations using the MM2 force field' clearly demonstrate the close resemblance of the twist half-chair conformation found in tetralins and the cyclohexene geometry (Table l), which was recognized in several earlier investigation^.^'^ Whereas substituents in the 2/3-position will be predominantly pseudoequatoria16b as in cyclohexene (see Table 1, footnote d), there is a major difference from cyclohexene for substituents at C-1/4 in tetralins, which are destabilized in the pseudoequatorial position by 'A1,'' interaction with the periplanar hydrogen at C-8 of the aromatic ring. Based on this and on detailed IR and NMR studies, Hanaya and other Japanese worked concluded that 1-substituents, in particular hydroxyl groups, usually dominate in a pseudoaxial position. Four lines of evidence, however, point to an almost equal population of eq and ax conformers in 1- ' Electron diffraction results:

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Carbon‐13 NMR analysis of cyclobutane dimers from benzocycloalkenes

Cited by 6 publications

References 14 publications

1,2,3,4,4a,5,8,8a‐Octahydro‐4β,8aα‐dimethylnaphthalen‐4aβ‐ol ( = Dehydrogeosmin), a Novel Compound Occurring in the Flower Scent of Various Species of cactaceae

1,2,3,4,4a,5,8,8a‐Octahydro‐4β,8aα‐dimethylnaphthalen‐4aβ‐ol ( = Dehydrogeosmin), a Novel Compound Occurring in the Flower Scent of Various Species of cactaceae

NMR Spectroscopy of Cyclobutanes

Conformations and ¹³C NMR shifts in tetralins

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Carbon‐13 NMR analysis of cyclobutane dimers from benzocycloalkenes

Cited by 6 publications

References 14 publications

1,2,3,4,4a,5,8,8a‐Octahydro‐4β,8aα‐dimethylnaphthalen‐4aβ‐ol ( = Dehydrogeosmin), a Novel Compound Occurring in the Flower Scent of Various Species of cactaceae

1,2,3,4,4a,5,8,8a‐Octahydro‐4β,8aα‐dimethylnaphthalen‐4aβ‐ol ( = Dehydrogeosmin), a Novel Compound Occurring in the Flower Scent of Various Species of cactaceae

NMR Spectroscopy of Cyclobutanes

Conformations and 13C NMR shifts in tetralins

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Conformations and ¹³C NMR shifts in tetralins