The synthesis of tricyclo[3.3.2.0f4]dec-2(4)-ene (3) has been attempted using a route analogous to those previously developed for 1 and 2. Complications were encountered in the synthesis. The confornational problems of the larger polycyclic structures in the synthesis of 3 must be more dfiicult to overcome than the increased angle strain of the smaller rings when 1 or 2 are synthesized.
2‐Chloronorbornene (I), derived from norcamphor by a known method, reacts with freshly prepared solutions of diiodomethane (II) and zinc/ copper couple to yield the cyclopropanation product (III).
125ChemInform Abstract The dibromide (VII), prepared as outlined in the reaction scheme, is treated with tert-butyllithium to give the strained cyclopropene (VIII) as an intermediate which is trapped by reaction with the benzofuran (IX), forming the cycloadduct (XI). (Yields given in mg).
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