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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 5
May 20, 1987 

Reaction of Methylenethioxanthene with Thiyl Radical: Formation of A Vinyl Sulfide
Eun Kyung Kim, Kyongtae Kim*, Jung Hyu Shin
Reactions of methylenethioxanthene (3) with n-propanethiol in the presence of di-t-butyl peroxide(DTBP) afforded preferentially propyl 9-thioxanthenylidenemethyl sulfide(8) rather than propyl 9-thioxanthenylmethyl sulfide(9) regardless of the concentration of n-propanethiol. On the other hand reactions of 3 with a low concentration of n-propanethiol in the presence of dibenzoyl peroxide(DBPO) gave 8, 1,2-bisthioxanthenylidene ethane(11), and thioxanthenylidenemethyl benzoate(12) but only 8 was formed at high concentration of the thiol. The formations of these products were rationallized by an electron transfer mechanism.
380 - 384
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