Partially fluorinated heterocyclic compounds. Part 24. [1] A plausible mechanism for the formation of the fischer indole product from acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone in which o-fluorine is lost
作者:Gerald M. Brooke
DOI:10.1016/s0022-1139(00)81061-1
日期:1988.7
Acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone (1) reacts in tetralin at reflux to give 4,5,6,7,8,9-hexafluoro-2-phenylbenz[e]indole (2) as the major product, accompanied by other materials including acetophenone 3,4,5,6,7,8-hexafluoro-2-naphthylhydrazone (4) which is proposed as the true precursor to the Fisher indole product (2) since it gives (2) under the same conditions. The presence
苯乙酮1,3,4,5,6,7,8-七氟-2-萘hydr在回流中在四氢萘中反应,得到4,5,6,7,8,9-六氟-2-苯基苯并[e]吲哚(2)为主要产品,并伴有其他材料,包括苯乙酮3,4,5,6,7,8-六氟-2-萘hydr(4),被提议为Fisher吲哚产品(2)的真正前体因为它在相同条件下给出(2)α四氢萘酮的在反应混合物中的存在提供了线索到还原消除的F -从(1)。