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(6′ RS ,8′ RS ,2 E )‐ und (6′ RS ,8′ SR ,2 E )‐3‐Methyl‐3‐(2y,2′,6′‐trimethyl‐7′‐oxabicyclo[4.3.0]non‐9′‐en‐8′‐yl)‐2‐propenal ([(5 RS ,8 RS )‐ und (5 RS ,8 SR )‐5,8‐Epoxy‐5,8‐dihydro‐ionyloinden]acetaldehyd): Synthese und Röntgenstrukturanalyse
Author(s) -
Acemoglu Murat,
Prewo Roland,
Bieri Jost Hans,
Eugster Conrad Hans
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670122
Subject(s) - chemistry , stereochemistry , crystal structure , acetaldehyde , medicinal chemistry , crystallography , organic chemistry , ethanol
Synthesis and X‐Ray Structure of (6′ RS ,8′ RS ,2 E )‐ and (6′ RS ,8′ SR ,2 E )‐3‐Methyl‐3‐(2′,2′,6′‐trimethyl‐7′‐oxabicyclo[4.3.0]non‐9′‐en‐8′‐yl)‐2‐propenal ([(5 RS ,8 RS )‐ and (5 RS ,8 SR )‐5,8‐Epoxy‐5,8‐dihydro‐ionylidene]acetaldehyde) To check our previous spectroscopic assignments of the structures of trans ‐ and cis ‐substituted furanoid end groups of carotenoid‐5,8‐epoxides, we now have synthesized the title compounds. An X‐ray structure determination of a single crystal of the trans ‐isomer (±)‐ ‐10A is in agreement with the 1 H‐NMR spectroscopic arguments: isomers with Δδ (HC(7), HC(8)) = 0.15–0.22 ppm and J > 1.4 for HC(7) belong to the cis ‐series; Δδ in trans ‐compounds is < 0.07 ppm, and HC(7) appears as a broad singulett.