Welcome to LookChem.com Sign In|Join Free

Article Doi

Generation of Thionitrosoarenes (ArN=S) from N-(Arylaminothio)phthalimides and in situ Trapping with Alkenes and Conjugated Dienes

DOI: 10.1039/P19900003225

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 3225 - 3235 (1990)

Update date:2022-09-26

Topics:

Authors:

Bryce, Martin R.Bryce, Martin R.

Taylor, Paul C.Taylor, Paul C.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19900003225

A series of N-(arylaminothio)phthalimide derivatives (7a-h) has been prepared by reaction of phthalimidesulphenyl chloride with the trimethylsilyl derivative of the appropriate arylamine.On treatment with triethylamine at room temperature, compounds (7) fragment to yield transient thionitroso species (8).Derivatives (8a-h) have been trapped in good yield as their Diels-Alder adducts with the following conjugated dienes: butadiene, 2.3-dimethylbutadiene, 1.4-diphenylbutadiene, (E,E)- and (E,Z)-hexa-2,4-diene, 1,1'-bicyclopentenyl (25) and 1,1'-bicyclohexenyl (26).The stereochemistry of the diene is retained in the adducts (19)-(24).Thionitrosoarene derivatives (8) also afford sulphenamide derivatives, e.g. (11) and (12)-(16), by ene addition to dimethylbutadiene, isobutene, and α-methylstyrene.N-Aryliminosulphur dichlorides (34) react with 2,3-dimethylbutadiene to yield 1,2-thiazine and sulphenamide products, probably by way of thionitrosoarene intermediates.

View More

Products guided by the article

Product name:2-(4-chlorophenyl)-3,6-dihydro-2H-1,2-thiazine

Cas No:132735-14-9

132735-14-9

R&D Labs maybe for 132735-14-9

Relevant to this article

Hot Product