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( E )‐3‐(1,3‐Dithian‐2‐yl)acroleine als geschützte Fumardialdehyde durch Oxopropenylierung des 1,3‐Dithians
Author(s) -
Rustemeier Klaus,
Breitmaier Eberhard
Publication year - 1982
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19821151223
Subject(s) - chemistry , dithiane , medicinal chemistry , nucleophile , stereochemistry , cleavage (geology) , stereoselectivity , catalysis , organic chemistry , geotechnical engineering , fracture (geology) , engineering
( E )‐3‐(1,3‐Dithian‐2‐yl)acroleins as Protected Fumardialdehydes via Oxopropenylation of 1,3‐Dithiane Lithiated 1,3‐dithiane 1 undergoes a stereoselective nucleophilic addition to 3‐ethoxyacroleins 2 yielding ( E )‐3‐(1,3‐dithian‐2‐yl)acroleins 5 . Upon oxidative cleavage with N ‐bromosuccinimide, these are convertible to the corresponding fumardialdehydes 6 , isolable as 2,4‐dinitrophenyl‐hydrazones 7 .