Dehalogenation of 1,3-diiodotricyclo[3.3.0.0(3,7)]octane: generation of 1,3-dehydrotricyclo[3.3.0.0(3,7)]octane, a 2,5-methano-bridged [2.2.1]propellane.
Compounds isolated from the reaction of (+/-)-1,3-diiodotricyclo[3.3.0.0(3,7)]octane with molten sodium or tBuLi suggest the intermediate formation of (+/-)-1,3-dehydrotricyclo[3.3.0.0(3,7)]octane. Worthy of note is the formation of stereoisomeric bi(5-methylenebicyclo[2.2.1]hept-2-ylidene) derivatives, probably by coupling of two units of (+/-)-1,3-dehydrotricyclo[3.3.0.0(3,7)]octane of the same or different absolute configuration followed by fragmentation, processes that have been studied by theoretical calculations.
Ayats
Carles
C
Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal 643, 08028 Barcelona, Spain.
Camps
Pelayo
P
Fernández
José A
JA
Vázquez
Santiago
S
D000465:Algorithms; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006219:Halogens / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D008956:Models, Chemical; D008962:Models, Theoretical; D009942:Organometallic Compounds / Q000737:chemistry; D012964:Sodium / Q000737:chemistry; D013237:Stereoisomerism; D020002:tert-Butyl Alcohol / Q000737:chemistry
C520078:1,3-dehydrotricyclo(3.3.0.0(3,7))octane; C520077:1,3-diiodotricyclo(3.3.0.0(3,7))octane; C520076:2,5-methano-bridged (2.2.1)propellane; D001952:Bridged-Ring Compounds; D006219:Halogens; D009942:Organometallic Compounds; D008094:Lithium; D012964:Sodium; D020002:tert-Butyl Alcohol