Details
| Original language | English |
|---|---|
| Pages (from-to) | 22-24 |
| Number of pages | 3 |
| Journal | SYNLETT |
| Issue number | 1 |
| Publication status | Published - Jan 1992 |
| Externally published | Yes |
Abstract
Tricyclo[5.3.0.0 2,6 ]deca-3,8-dienes (5) and -3,9-dienes (8) are obtained by Shapiro reactions from tosylhydrazones 4 (3,8-bis(tosylhydrazono)tricyclo[5.3.0.0 2,6 ]decanes) and 7 (3,10-bis(tosylhydrazono)tricyclo[5.3.0.0 2,6 ]decanes) in gram quantities. The tricyclo[5.3.0.0 2,6 ]deca-4,9-diene-3,8-dione bis(tosylhydrazone) (10) can be prepared in 49% yield from the known dienenone 9. Reaction of 10 with lithium bases does not lead to elimination products but gives dilithium salt 11. Differential scanning calorimetry (DSC) analysis shows a reaction of 11 above 120 °C. Trapping with dimethyl fumarate leads to the new double spiro-annulated pentacycle 13a,b (2′,2″,3′,3″- tetramethoxycarbonyldispiro [tricyclo[5.3.0.0 2,6 ]deca-4,9-diene-3,8-dicyclopropane]). Trapping with iron pentacarbonyl generates fulvalene-diiron complex 14 [tetracarbonyl(η 5 :η 5 -pentafulvalene)diiron] as the result of an elimination/isomerisation sequence.
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: SYNLETT, No. 1, 01.1992, p. 22-24.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis and Reactions of Some Tosylhydrazones of Tricyclo [53.0.0 2,6 ] decadiones
AU - Bister, Hans Jürgen
AU - Butenschön, Holger
PY - 1992/1
Y1 - 1992/1
N2 - Tricyclo[5.3.0.0 2,6 ]deca-3,8-dienes (5) and -3,9-dienes (8) are obtained by Shapiro reactions from tosylhydrazones 4 (3,8-bis(tosylhydrazono)tricyclo[5.3.0.0 2,6 ]decanes) and 7 (3,10-bis(tosylhydrazono)tricyclo[5.3.0.0 2,6 ]decanes) in gram quantities. The tricyclo[5.3.0.0 2,6 ]deca-4,9-diene-3,8-dione bis(tosylhydrazone) (10) can be prepared in 49% yield from the known dienenone 9. Reaction of 10 with lithium bases does not lead to elimination products but gives dilithium salt 11. Differential scanning calorimetry (DSC) analysis shows a reaction of 11 above 120 °C. Trapping with dimethyl fumarate leads to the new double spiro-annulated pentacycle 13a,b (2′,2″,3′,3″- tetramethoxycarbonyldispiro [tricyclo[5.3.0.0 2,6 ]deca-4,9-diene-3,8-dicyclopropane]). Trapping with iron pentacarbonyl generates fulvalene-diiron complex 14 [tetracarbonyl(η 5 :η 5 -pentafulvalene)diiron] as the result of an elimination/isomerisation sequence.
AB - Tricyclo[5.3.0.0 2,6 ]deca-3,8-dienes (5) and -3,9-dienes (8) are obtained by Shapiro reactions from tosylhydrazones 4 (3,8-bis(tosylhydrazono)tricyclo[5.3.0.0 2,6 ]decanes) and 7 (3,10-bis(tosylhydrazono)tricyclo[5.3.0.0 2,6 ]decanes) in gram quantities. The tricyclo[5.3.0.0 2,6 ]deca-4,9-diene-3,8-dione bis(tosylhydrazone) (10) can be prepared in 49% yield from the known dienenone 9. Reaction of 10 with lithium bases does not lead to elimination products but gives dilithium salt 11. Differential scanning calorimetry (DSC) analysis shows a reaction of 11 above 120 °C. Trapping with dimethyl fumarate leads to the new double spiro-annulated pentacycle 13a,b (2′,2″,3′,3″- tetramethoxycarbonyldispiro [tricyclo[5.3.0.0 2,6 ]deca-4,9-diene-3,8-dicyclopropane]). Trapping with iron pentacarbonyl generates fulvalene-diiron complex 14 [tetracarbonyl(η 5 :η 5 -pentafulvalene)diiron] as the result of an elimination/isomerisation sequence.
UR - http://www.scopus.com/inward/record.url?scp=85022237757&partnerID=8YFLogxK
U2 - 10.1055/s-1992-21251
DO - 10.1055/s-1992-21251
M3 - Article
AN - SCOPUS:85022237757
SP - 22
EP - 24
JO - SYNLETT
JF - SYNLETT
SN - 0936-5214
IS - 1
ER -