Title

Naphthoquinone: Reactions with Alkanedithiol

Authors

Tom Lam

Document Type

Article

Publication Date

2006

Abstract

Here we studied the reactions between various 1,4-naphthoquinones and alkanedithiols, namely, 1,2-ethanedithiol and 1,3-propanedithiol. The 1,4-naphthoquinone derivatives examined were 2-bromo-, 2,3-dibromo-, 2-chloro-, 2,3-dichloro, 2-bromo-3-methoxy-, 2-methoxy-1,4-naphthoquinone and 1,4 naphthoquinone itself. All of these 1,4-naphthoquinones are potentially expected to go through substitution reactions. We identified two groups of substitution products. In the reactions with 1,2-ehtanedithiol, for example, a ?cyclic product?, 2,3-dihydro-1,4-dithia-9,10-anthracenedione, and a ?spiro product?, 2-1?,3?-dithiacyclopentane spiro 2?-2,3-dihydro-1,4-naphthoquinone or its 3-halogeno-derivative. The formation of these two groups of products, a ?cyclic product? and a ?spiro product,? were found to depend upon the substituents on the 2- and/or 3-positions of 1,4-naphthoquinones as well as the reaction medium, be it acidic, neutral, or basic. This observation strongly indicates that different mechanisms are involved in the substitution reactions.

Advisor

Tetsuo Otsuki

Department

chem

Support

C. David West Fellowship

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