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Generation and reactivity of sterically hindered bicyclo[3.1.0]hex-1-enes

✍ Scribed by Richard F. Salinaro; Jerome A. Berson

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
224 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

Z-t-Butylbicyclo[3.1.O]hex-1-ene dimerizes primarily by a [o + IT] way, whereas 2,5-di-t-butylbicyclo[3.l.O]hex-1-ene undergoes an unusual hydrogen shift reaction to 1,3-di-t-butyl-2-methylcyclopentadiene. The presence of bulky substituents on or near the strained double bond of a bicyclo[3.l.O]hex-1-ene (1) should decrease the olefin's reactivity in [II + -

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✍ Hee-Yoon Lee; Yeonjoon Kim; Yong-Han Lee; Byung Gyu Kim πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 67 KB

Anions of allylmeldrum's acids reacted with phenyl(propynyl)iodonium salt to produce bicyclo[3.1.0]hex-1-enes as the reactive intermediates through cyclopropanation reaction to yield various dimerization products. Depending on the substitution pattern on the intermediates, various dimeric products w