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Synthesis and reactions of 3,4-di-t-butylthiophene

✍ Scribed by Juzo Nakayama; Shoji Yamaoka; Masamatsu Hoshino

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
235 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Di-g-butylthiophene (1) was surprisingly easily synthesized from readily accessible bis(Z-t-butyl-2-oxoethyl) sulfide (2).

Reactions of 1 with a variety of electrophiles were examined.

Sterically overcrowded 3,4-di-t-butylthiophene (1) was first synthesized in 19801 after numerous unsuccessful attempts. 2 .. X-Ray crystal-structure determination shows that the internal strain in this molecule is appreciable.3

Although this provokes an interest in the reactivities of this compound, such study has not appeared. Herein we report a surprisingly facile synthesis of 1 and its reactions with a variety of electrophiles.

-.

We have recently developed a new thiophene synthesis, which involves intramolecular reductive coupling of a,9' -diketo sulfides and the acid-catalyzed dehydration of the resulting 3,4-dihydroxythiolanes. 4 Application of this thiophene synthesis to readily obtainable bis(Z-t-butyl-2-oxoethyl) sulfide (2)' allows a simple synthesis of 1. Thus, treatment of 2 with a lowvalent tiianium reagent, prepared from titanium(IV) chloride and zinc powder,6 in tetrahydrogfuran (THF) affords +-3,4-di-t-butyl-3,4_dihydroxythiolane (3)7 in 53% yield. The cis-configuration of this diol was established by X-ray-2 3 89%

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