125013-84-5Relevant articles and documents
SYNTHESIS OF ADDUCTS OF DIHALOGENOCARBENES WITH THE DIMERS OF CYCLOPENTADIENE AND SPIROHEPTA-4,6-DIENE AND THEIR THERMAL TRANSFORMATIONS
Molchanov, A. P.,Pecheritsyna, Ya. P.,Kostikov, R. R.
, p. 1076 - 1081 (2007/10/02)
It was found that dichloro-, dibromo-, bromochloro-, and bromofluorocarbenes react with the cyclopentadiene dimer (tricyclo2,6>deca-3,8-diene) and the spirohepta-4,6-diene dimer cyclopropanespiro-5-(tricyclo2,6>deca-3,8-diene)-10-spirocyclopropane with the exclusive formation of the adducts at the double bond of the cyclopentene fragment, i.e., 4,4-dihalogenotetracyclo2,7.03,5>undec-5-enes and cyclopropanespiro-6-(4,4-dihalogenotetracyclo2,7.03,5>undec-9-ene)-11-spirocyclopropanes respectively.When the adducts of the carbenes are heated with the cyclopentadiene dimer, they undergo thermal isomerization with opening of the three-membered ring, leading to 4,5-dihalogenotricyclo2,7>undeca-3,9-dienes.The adducts of the carbenes with the spirohepta-4,6-diene dimer undergo the reverse Diels-Alder reaction when heated with the formation of cyclopropanespiro-5-(tricyclo2,6>deca-3,8-diene)-10-spirocyclopropane and 3-(2-halogenoethyl)halogenobenzenes.