712-25-4Relevant articles and documents
The clemmensen reduction of pentacyclo [6.4.0.02,7.03,11.0 6,10]dodecane-9,12-dione
Martins,Fourie,Venter,Wessels
, p. 623 - 632 (1990)
The Clemmensen reduction of pentacyclo[6.4.0.02,7.03,11.0 6,10]= dodecane-9,12-dione unexpectedly led to the formation of pentacyclo[6.4.0. 02,6.05,9.04, 12]-2-dodecanol and pentacyclo[6.4.0.02,7.03,11.0 6,10]dode= cane-1,8-diol as main products. Tetracyclo[6.4.0.05,9.0412dodecane-2,7-dione and its corresponding hemiacetal were obtained as byproduc structures of the Clemmensen products were elucidated from an extensive 1H and 13C n.m.r. study.
The influence of hydrate formation on the Clemmensen reduction of pentacyclo [5.4.0.02,6;03,10;05,9]undecane-8,11-dione and pentacyclo[6.4.0.02,7.03,11.06,10]dodecane-9,
Martins,Viljoen,Coetzee,Fourie,Wessels
, p. 9215 - 9224 (2007/10/02)
Hydration of pentacyclo [5.4.0.02,6,03,10.05,9]undecane-8,11-dione led to the formation of a mixture of a geminal diol (80%) and a transannular hydrate (20%) and not to only the latter as previously accepted. Compounds with smaller intercarbonylic distances formed only transannular hydrates which promoted rearrangement reactions during Clemmensen reduction. The transannular hydrate of pentacyclo [6.4.0.02,7.03,11.06,10]dodecane-9,12-dione produced pentacyclo [6.4.0.02,6.05,9.04,12]-2-dodecanol.
