
TY  - JOUR
A1  - Kagi, RI 
A1  - Johnson, BL 
T1  - Substituted <I>endo</I>-Tricyclo[3,2,1,0<sup>2,4</sup>]oct-6-enes. I. Preparation by the Diels-Alder reaction between cyclopropene and substituted cyclopentadienes
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1975
VL  - 28
IS  - 10
SP  - 2175
EP  - 2187
KW  - 
UR  - https://doi.org/10.1071/CH9752175 
N2  - The Diels-Alder reaction between cyclopropene and substituted cyclopentadienes has been used to prepare several chloro- and chloromethoxy-substituted endo-tricyclo[3,2,1,02,4]oct-6-enes. In the presence of base, the reaction of 1,2,3,4-tetrachlorocyclopentadiene with cyclopropene yielded the expected adduct together with adducts arising from the isomeric 1,2,3,5- and 1,2,4,5-tetrachlorocyclo- pentadienes. Subsequent isomerization during workup of the adduct, 1,6,7,anti-8-tetrachloro-endo-tricyclo[3,2,1,02,4]oct-6-ene, afforded endo-4,6,7,8-tetrachlorotricyclo[3,3,0,02,8]oct-6-ene. The relatively unreactive methoxy-substituted cyclopentadienes yielded adducts of cyclopropene together with adducts of 3-cyclopropylcyclopropene (cyclopropene dimer). Structural assignments of adducts were based predominantly on p.m.r. data which will be discussed in greater detail in a later publication. 
ER  -

