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Conformational effects observed in an N.M.R. study of [7](2.6)dithiametacyclophane

✍ Scribed by R.H. Mitchell; V. Boekelheide

Book ID
104239399
Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
195 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

The recent report by Vogtie (2) on the synthesis and a temperaturedependent n .m .r . study of [8J(2 .7)dithiametacyclophane prompts us to report our results on the analogous, smaller-ring compound, c7J(2 .6)dithiametacyclophane (I) .

Originally, I was obtained, quite unexpectedly, in 18% yield m-xylylene dibromide to a solution of the bis-dithiane III (3) and lithium in tetrahydrofuran . Although the mechanism for the formation of I in this reaction is not clear, its structure was confirmed by independent synthesis through the reaction of m-xylylene dibromide with the dianion of propane-l,3-dithiol . The latter reaction gave I in 43% yield, together with the expected dieter II, formed in 10% yield . Aside from its independent synthesis, the structure of the metacyclophane I a (m .p . 105-106°) was indicated by its n .m .r . spectrum (in CD2C1 2 at room temperature) : a 1H singlet IE a

All new compounds showed satisfactory elemental analyses .

2013

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