The Reaction of Saccharin Derivatives with N,N-Diethylprop-1-ynamine: Formation of Cyclobutenyl Saccharinates and of a Spiro-oxete

DOI: 10.1039/c39840001583

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 1583 - 1584 (1984)

Update date:2022-08-10

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Authors:

Abramovitch, Rudolph A.

Ooi, Gino H. C.

Sun, Han-Li

Pierrot, Marcel

Baldy, Andre

Estienne, Jacques

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Article abstract of DOI:10.1039/c39840001583

Saccharin and two equivalents of N,N-diethylprop-1-ynamine give a cyclobutenyl saccharinate (4) which, on bromination, gives the N-(cyclobutenyl cation)saccharin derivative (8), whose structure was established by X-ray crystallography ; N-methylsaccharin reacts with one equivalent of ynamine to yield the spiro-oxete (9): this represents the second isolation of such a stable oxete from reaction of an ynamine with a carbonyl group.

Full text of DOI:10.1039/c39840001583

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