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Durham e-Theses
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Generation and reactions of aryl and alkyl thionitroso compounds

Heaton, Julie N. (1992) Generation and reactions of aryl and alkyl thionitroso compounds. Doctoral thesis, Durham University.

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Abstract

Transient thionitrosoarenes (102) with para substituents have been generated from N-(arylaminothio)-phthalimide derivatives (101) and intercepted with chloroprene and piperylene to give regioisomeric Diels- Alder adducts. Reaction of thionitrosoarenes (102) with 1-methylcyclohexene, a-pinene and β-pinene gave sulphenamides. Sulphenamides (110) and(123) have been reacted with 2,6-difluorobenzoylisocyanate. Heteroaryl thionitroso compounds have been prepared. Thionitrosoarenes with an ortho substituent have been generated via two different routes and trapped with 2,3-dimethyl-l,3-butadiene to give mixtures of Diels-Alder and ene adducts; the ene adduct was the major isomer for each system. Thionitrosoarene (159b) was generated from 3- aminobenzisothiazole (157b) using lead tetraacetate and was intercepted with 2,3-dimethyl-l,3-butadiene to give Diels-Alder (160) and ene (161) adducts. Thionitrosoalkanes have been generated using two different routes and trapped with 2,3-dimethyl-l,3-butadiene to give Diels-Alder and ene adducts.

Item Type:Thesis (Doctoral)
Award:Doctor of Philosophy
Thesis Date:1992
Copyright:Copyright of this thesis is held by the author
Deposited On:18 Dec 2012 12:05

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