Synthesis and conformation of 6,8,10-trinitro-1,4-dioxaspiro[4.5]decane
โ Scribed by Yu. M. Atroshchenko; S. S. Golotvin; I. V. Shakhkel'dyan; O. V. Shishkin; Zh. O. Lavrik; O. Ya. Borbulevych; M. Yu. Antipin; E. N. Alifanova; S. S. Gitis; I. V. Ivanov; A. Ya. Kaminsky
- Publisher
- Springer
- Year
- 1999
- Tongue
- English
- Weight
- 391 KB
- Volume
- 48
- Category
- Article
- ISSN
- 1573-9171
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Acid-catalyzed equilibration of spiroketals 5SHp6 and 55Haj3 involves a two stage process whereby the 1,6-dioxaspiro]4.4]nonanes can be equilibrated under mild conditions to a pair of 1,6\_dioxaspiro[45]decanes with preservation of the adjacent C-20 methyl stereocenter. Under more forcing conditions
L. gave the gas chromatogram shown below [2]. Using a GC/MS-coupling system (Varian MAT 311A), in addition to nonanone-2, the spiroketals 1-4 could be 9 identified, all of which occurred as pairs of diastereomers [3]. According to [4], authentic samples were prepared for comparison.