Dimetalation of isopropenylacetylene. Application in the synthesis of 3-methylselenophen, 3-methylene-2, 3-dihydroselenophen and the tellurium analogues

W Kulik, HD Verkruijsse, RLP De Jong, H Hommes…

Index: Kulik, W.; Verkruijsse, H. D.; Jong, R. L. P. de; Hommes, H.; Brandsma, L. Tetrahedron Letters, 1983 , vol. 24, # 21 p. 2203 - 2204

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Citation Number: 21

Abstract

Abstract Reaction of the dilithio derivative of isopropenylacetylene with one equivalent of selenium or tellurium, followed by addition of t-BuOH and HMPT gives 3-methylene-2, 3- dihydroselenophen and 3-methylselenophen or 3-methylene-2, 3-dihydrotellurophen in reasonable yields. The latter compound can be converted into 3-methyltellurophen by treatment with t-BuOK in HMPT.

 Related Synthetic Route
Structure

87221-58-7

~%

3-methylselenophene Structure

7559-43-5

3-methylselenophene

2-Metbut-1-en-1yne Structure

78-80-8

2-Metbut-1-en-1yne

~%

3-methylselenophene Structure

7559-43-5

3-methylselenophene

3-methylene-2,3-dihydrotellurophene Structure

87221-59-8

3-methylene-2,3...

~87%

3-methyltellurophene Structure

87221-61-2

3-methyltellurophene

Structure

87221-58-7

~%

3-methyltellurophene Structure

87221-61-2

3-methyltellurophene

2-Metbut-1-en-1yne Structure

78-80-8

2-Metbut-1-en-1yne

~%

3-methyltellurophene Structure

87221-61-2

3-methyltellurophene


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