( E )‐3‐(1,3‐Dithian‐2‐yl)acroleine als geschützte Fumardialdehyde durch Oxopropenylierung des 1,3‐Dithians | Zendy

Rustemeier Klaus | Zendy; Breitmaier Eberhard | Zendy

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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 .

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