Some reactions of butadienylsulfonium salts with alkali hydroxide, thiophenolate, and alkoxides are described. With catalytic amounts of alkoxide in alcoholic solution the dienylsulfonium salts 1 a, b yield (2,4-dialkoxybutyl)sulfonium salts 7 and/or (alkoxybuteny1)-sulfonium salts 4 and 6. At high alkoxide concentration the main products are substituted butenyl sulfides 9, formed by [2,3]-sigmatropic rearrangement of the 4-ylides. Under the same conditions (2,3-dimethyl-1,3-butadienyl)dimethylsulfonium bromide (1 c) rearranges to 2-methyl-3-rnethylene-5-methylthio-l-pentene (16).Wir haben kurzlich uber die Darstellung von trans-Dialkyl-(1,3-butadienyl)sulfoniumhalogeniden 1 berichtet 1) und beschreiben im folgenden ihr Reaktionsverhalten gegenuber Basen.
6 a ) . The spectra of ( 3 a ) , ( 2 a ) , and chlorobutatriene['] were used for comparison.The ' 3C-NMR spectrum confirmed the structural proposal, in particular on comparison with the spectrum of butatrienef4! The UV spectrum [hm,,(ethanol)=258nm (E>, lo4) also accords with the structure given. The spectra of butatrienec5] and ( 2 a ) , PF6 instead of Cltb1, were used for comparison.
Die Sulfoniumsalze (Ia) bzw. (Ib) reagieren in alkoholischer Lösung in Gegenwart katalytischer Mengen der Alkoholate (II) zu den Dialkoxyderivaten (III) l und/oder den Monoalkoxyderivaten (IV) und (V).
Das Disulfoniumchlorid (I) liefert bei Behandlung mit Na‐methanolat in Methanol bei ‐40°C das Butatrienylsulfoniumchlorid (II), dessen Struktur aus den NMR‐Spektren abgeleitet wird.
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