Dihydropyran cycloadducts. Part 4. X-ray and 13C nuclear magnetic resonance studies on 2-methyl-9-phenyl-4a-pyrrolidin-1-yl-1,2,3,4,4a,- 5,6,7,8,9a-decahydroxanthen

György Oszbach, Dezsö Szabó, G. Argay, A. Kálmán, András Neszmélyi

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Based on X-ray data the relative configurations in the title compound are as follows: the cyclohexane and dihydropyran rings are cis-fused and the 9-phenyl group is cis to the annelated hydrogen atom. This is the first evidence for previous assumptions that the ring closure of cyclic enamines with heterodiene systems results in a cis-ring junction. However, the position of the 9-phenyl group is in contrast to earlier results, established by 1H n.m.r. and chemical methods. The products from the reaction of different cyclic enamines with 2-benzylidenecyclohexanone show the same stereochemistry according to 13C n.m.r. investigations.

Original languageEnglish
Pages (from-to)447-451
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number4
DOIs
Publication statusPublished - 1983

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Stereochemistry
Hydrogen
Nuclear magnetic resonance
X rays
Atoms
Cyclohexane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Dihydropyran cycloadducts. Part 4. X-ray and 13C nuclear magnetic resonance studies on 2-methyl-9-phenyl-4a-pyrrolidin-1-yl-1,2,3,4,4a,- 5,6,7,8,9a-decahydroxanthen",
abstract = "Based on X-ray data the relative configurations in the title compound are as follows: the cyclohexane and dihydropyran rings are cis-fused and the 9-phenyl group is cis to the annelated hydrogen atom. This is the first evidence for previous assumptions that the ring closure of cyclic enamines with heterodiene systems results in a cis-ring junction. However, the position of the 9-phenyl group is in contrast to earlier results, established by 1H n.m.r. and chemical methods. The products from the reaction of different cyclic enamines with 2-benzylidenecyclohexanone show the same stereochemistry according to 13C n.m.r. investigations.",
author = "Gy{\"o}rgy Oszbach and Dezs{\"o} Szab{\'o} and G. Argay and A. K{\'a}lm{\'a}n and Andr{\'a}s Neszm{\'e}lyi",
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journal = "Journal of the Chemical Society, Perkin Transactions 2",
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TY - JOUR

T1 - Dihydropyran cycloadducts. Part 4. X-ray and 13C nuclear magnetic resonance studies on 2-methyl-9-phenyl-4a-pyrrolidin-1-yl-1,2,3,4,4a,- 5,6,7,8,9a-decahydroxanthen

AU - Oszbach, György

AU - Szabó, Dezsö

AU - Argay, G.

AU - Kálmán, A.

AU - Neszmélyi, András

PY - 1983

Y1 - 1983

N2 - Based on X-ray data the relative configurations in the title compound are as follows: the cyclohexane and dihydropyran rings are cis-fused and the 9-phenyl group is cis to the annelated hydrogen atom. This is the first evidence for previous assumptions that the ring closure of cyclic enamines with heterodiene systems results in a cis-ring junction. However, the position of the 9-phenyl group is in contrast to earlier results, established by 1H n.m.r. and chemical methods. The products from the reaction of different cyclic enamines with 2-benzylidenecyclohexanone show the same stereochemistry according to 13C n.m.r. investigations.

AB - Based on X-ray data the relative configurations in the title compound are as follows: the cyclohexane and dihydropyran rings are cis-fused and the 9-phenyl group is cis to the annelated hydrogen atom. This is the first evidence for previous assumptions that the ring closure of cyclic enamines with heterodiene systems results in a cis-ring junction. However, the position of the 9-phenyl group is in contrast to earlier results, established by 1H n.m.r. and chemical methods. The products from the reaction of different cyclic enamines with 2-benzylidenecyclohexanone show the same stereochemistry according to 13C n.m.r. investigations.

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