The Chemistry of Ortho-Mercaptoazo Compounds

Burawoy, A.

doi:10.1016/b978-1-4831-9982-5.50028-2

Organic Sulfur Compounds 1961

DOI: 10.1016/b978-1-4831-9982-5.50028-2

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The Chemistry of Ortho-Mercaptoazo Compounds

A. Burawoy

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1978

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Intramolekulare Substitution von Sulfensäure‐allylestern

Hoffmann

Goldmann

1978

Chem. Ber.

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Intramolecular Thiophilic Substitution on Ally1 SulfenatesThe sulfoxides 8a, b and 13a, b possess a mechanism for self-destruction: As soon as a [2,3]-sigmatropic rearrangement to the sulfenates 14a, b and 17a, b, respectively, occurs, which is otherwise reversible, a rapid cleavage of the molecule ensues by intramolecular thiophilic substitution liberating ally1 alcohol.Mislow ') fand, daB Allylsulfoxide (1) uber eine [2,3]-sigmatrope Umlagerung mit Sulfensaureallylestern (2) im Gleichgewicht stehen. Vereinzelte Beobachtungen ' ) zeigten, daB sich der Sulfensaureester aus dem Gleichgewicht heraus mit thiophilen Reagenzien zu Allylalkoholen spalten 1aBt. Evans3' erkannte darin eine praparative Methode zur Darstellung von Allylalkoholen, die rasch breite Anwendung fand 4).

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Intramolekulare Substitution von Sulfensäure‐allylestern

Hoffmann

Goldmann

1978

Chem. Ber.

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The Chemistry of Ortho-Mercaptoazo Compounds

Cited by 1 publication

References 35 publications

Intramolekulare Substitution von Sulfensäure‐allylestern

Intramolekulare Substitution von Sulfensäure‐allylestern

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