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Studies in the cycloproparene series: Approaches to octahydrocyclopropa[l]phenanthrenes

Journal Article


Abstract


  • Cycloaddition between 1, 1ˊ-bicyclohexenyl (3) and the perhalocyclopropenes (4) affords the 1a, 1b, 2, -3, 4, 5, 6, 7, 8, 9, 9a, 9b-dodecahydrocyclopropa[l]phenanthrenes (5). Whilst halides (5a, b) are resistant to dehydrohalogenation, the difluoro derivatives (5c, d) yield 1, 2, 3, 4, 5, 6, 7, 8-octahydrophenanthrene-9-carbaldehyde (12) with base. Under debromination conditions compound (5d) is converted into 1, 2, 3, 4, 5, 6, 7, 8, 8a, 10a-decahydrophenanthrene-9-carboxylic acid (14) probably by way of the ring-strained cyclopropene (9). © 1983, CSIRO. All rights reserved.

Publication Date


  • 1983

Citation


  • Halton, B., & Officer, D. L. (1983). Studies in the cycloproparene series: Approaches to octahydrocyclopropa[l]phenanthrenes. Australian Journal of Chemistry, 36(6), 1291-1297. doi:10.1071/CH9831291

Scopus Eid


  • 2-s2.0-84970607828

Start Page


  • 1291

End Page


  • 1297

Volume


  • 36

Issue


  • 6

Abstract


  • Cycloaddition between 1, 1ˊ-bicyclohexenyl (3) and the perhalocyclopropenes (4) affords the 1a, 1b, 2, -3, 4, 5, 6, 7, 8, 9, 9a, 9b-dodecahydrocyclopropa[l]phenanthrenes (5). Whilst halides (5a, b) are resistant to dehydrohalogenation, the difluoro derivatives (5c, d) yield 1, 2, 3, 4, 5, 6, 7, 8-octahydrophenanthrene-9-carbaldehyde (12) with base. Under debromination conditions compound (5d) is converted into 1, 2, 3, 4, 5, 6, 7, 8, 8a, 10a-decahydrophenanthrene-9-carboxylic acid (14) probably by way of the ring-strained cyclopropene (9). © 1983, CSIRO. All rights reserved.

Publication Date


  • 1983

Citation


  • Halton, B., & Officer, D. L. (1983). Studies in the cycloproparene series: Approaches to octahydrocyclopropa[l]phenanthrenes. Australian Journal of Chemistry, 36(6), 1291-1297. doi:10.1071/CH9831291

Scopus Eid


  • 2-s2.0-84970607828

Start Page


  • 1291

End Page


  • 1297

Volume


  • 36

Issue


  • 6