Chapter 6. Alicycles

Cuban

Eaton

text.

Table 6-1. Eaton synthesis of cuban

Molecular structuresReaction description

  • +Br2\H+.

  • enol formation, than attack of the enol with +Br2

  • carbonyl group in the alpha-bromo-keton is less basic, the enolisation will proceed 'only', if all alpha-halogenketon molecules are exhausted (the Section called Halogenisation in Chapter 2)

  • Basic medium

  • -HBr

  • +Br2

  • +Et2NH

  • -2 HBr

  • secondary orbital interactions explains endo product

  • cyclopentadien is planar. In the intermediate transition state an envelope conformation can be supposed

  • Diels-Alder-Reaction, , supra-supra-facial cyclo-addition

  • Ketalisation using ethylenglykol

  • , photochemical allowed

  • +SOCl2, halogenisation of the acidic group

  • +tert-pentyl-carbon-acid

  • -CO2, -tert-pentyl-carbon-acid

  • +H2SO4, hydrolisis of the ketal

 

Pettit

text.