Journal of organometallic chemistry

Syntheses with organoboranes. IX. Vinyl-and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels–Alder reaction

M Zaidlewicz, JR Binkul, W Sokół

Index: Zaidlewicz, Marek; Binkul, Jacek R.; Sokol, Wojciech Journal of Organometallic Chemistry, 1999 , vol. 580, # 2 p. 354 - 362

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Citation Number: 18

Abstract

Vinyl-and 1-alkenyldichloroboranes were used as dienophiles for the Diels–Alder reaction with representative aliphatic and cyclic 1, 3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation–mesylation– reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride produced pure olefins in good ...

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