27714-83-6Relevant academic research and scientific papers
Studies in the Cycloproparene Series: Approaches to Bicycloocta-1,3,6-triene, a Cyclopropa-Fused Cycloheptatriene
Halton, Brian,Russell, Sarah G. G.
, p. 1069 - 1076 (2007/10/02)
The dichloromethylene-bridged annulene (5) is available in four steps (47percent) from 1,4,5,8-tetrahydronaphthalene (11) via the dibromide (15); the minor (5percent) product of dehydrobromination of (15) is 2-bromo-9,9-dichloro-1,4-dihydro-4a,8a-methanonaphthalene (16).Dichlorocarbene adds to the norcaradiene form of (5) to give adduct (6) with 80percent efficiency.Diene (6) resists both ?4 + ?2> cycloadditions and reductive dechlorination.Neither (5) nor parent 1,6-methanoannulene (18) adds methylene from Simmons-Smith cyclopropanation procedures.
Studies in the Cycloproparene Series: Attempted Cycloadditions with Tricyclo3,5>dodeca-2,5,7,9,11-pentaene
Halton, Brian,Russell, Sarah G. G.
, p. 911 - 917 (2007/10/02)
4,4-Dichlorotricyclo3,5>dodeca-7,9,11-triene (18a) undergoes cycloaddition with 4-phenyl-1,2,4-triazoline-3,5-dione via its norcaradiene valence-bond isomer (18b) to give adduct (21) in 86percent yield.By comparison the aromatic tricyclo3,5>dodeca-2,5,7,9,11-pentaene (6) and its 12-chloro stereoisomer (20) fail to react; this contrasts with the behaviour of other 1,6-methanoannulene derivatives.
