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Synthesis and rearrangement of dispiro[3.1.3.2]-, dispiro[3.0.3.3]- and dispiro[3.0.4.2]undecanes- new entries to [3.3.3]propellanes

✍ Scribed by Lutz Fitjer; Andrew Kanschik; Marita Majewski

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
996 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

The dispiroketones 46 have been synthesized and rearranged by treatment with acids yielding the bicyclic enone 36 under kinetic control and the [3.3.3]propellane 37 under thermodynamic control. The corresponding alcohols 10-12 all yield the [3.3.3]propeUane 41. The rearrangement of [7,7-D2)-12 to [8,8-D&41 proweds ste~speeifidy and ints potential precursor of (f)-modhephene 43. Likewise, dispiranes 44 and 4r

to dispixane 42 as are potential precursors of (*)-isocomene 45.

πŸ“œ SIMILAR VOLUMES

Syntheses of dispiro[2.1.4.1]decane and
Syntheses of dispiro[2.1.4.1]decane and dispiro[2.0.3.3]decane
✍ John E Baldwin; Maryann E Keene; Rajesh Shukla πŸ“‚ Article πŸ“… 2000 πŸ› Elsevier Science 🌐 French βš– 53 KB

Efficient syntheses of the hitherto unknown hydrocarbons dispiro[2.1.4.1]decane and dispiro-[2.0.3.3]decane have been realized through reaction sequences involving spiro[3.4]octan-2-one and spiro[3.4]octan-5-one as key intermediates.

ChemInform Abstract: Syntheses of Dispir
ChemInform Abstract: Syntheses of Dispiro[2.1.4.1]decane and Dispiro[2.0.3.3]decane.
✍ John E. Baldwin; Maryann E. Keene; Rajesh Shukla πŸ“‚ Article πŸ“… 2001 πŸ› John Wiley and Sons βš– 28 KB πŸ‘ 1 views

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