Iodocyclization of (Z)-1-(Butyltelluro)-1, 4-diorganylbut-1-en-3-ynes. Synthesis and Reactions of 3-Iodotellurophenes

…, MA Pereira, J Zukerman-Schpector

Index: Dabdoub, Miguel J.; Dabdoub, Vania B.; Pereira, Marco A.; Zukerman-Schpector, Julio Journal of Organic Chemistry, 1996 , vol. 61, # 26 p. 9503 - 9511

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Citation Number: 41

Abstract

The iodocyclization of (Z)-tellurobutenynes 5a-g by reaction with I2/petroleum ether was studied in detail. 3-Iodotellurophenes 7a-f were formed, and optimum conditions to obtain these compounds in high yields were established. The reaction involves attack of iodide at the initially formed intermediate of type 10 followed by ring closure that is favored by the strong aromatic character of the resulting products. Two possible and alternative pathways ...