Cycloadditions of Isoquinolinium Salts: Vinyl Sulfide Dienophiles for the Syntheses of 1-Naphthaldehydes and Tetralins

DOI: 10.1021/jo00266a019

Source and publish data:

Journal of Organic Chemistry p. 1097 - 1101 (1989)

Update date:2022-08-04

Topics:

Authors:

Gupta, Ram B.

Franck, Richard W.

Onan, Kay D.

Soll, Clifford E.

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Article abstract of DOI:10.1021/jo00266a019

Vinyl sulfides are used as dienophiles in the Bradsher cycloaddition reaction.Processing of the cycloadducts leads to either tetralins or naphthaldehydes.The tetralins are formed with high stereoselectivity.The configuration of the products is confirmed by an X-ray structure determination.Removal of sulfur from the tetralin products affords materials that are the equivalent of having used simple alkenes as dienophiles.

Full text of DOI:10.1021/jo00266a019

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