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Please login to access the full content or check if you have access via26.2.1.1.1 Variation 1: From 1,3-Dithiane
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Salaün, J., Science of Synthesis, (2005) 26, 557.
5,9-Dithiaspiro[3.5]nonane (2) is formed in 65–84% yield from the reaction of the 2-lithiated derivative of 1,3-dithiane (1)[7] with 1-bromo-3-chloropropane, followed by butyllithium-induced cyclization of the resulting 2-(3-chloropropyl)-1,3-dithiane intermediate. Cyclobutanone (3) is obtained in 60–81% yield after the protecting group of cyclobutanone dithioacetal 2 has been cleaved by treatment with an excess of mercury(II) chloride in triethylene glycol and water (Scheme 1).[8] Use of 1,3-dibromopropane is unsuitable because it entails the formation of cyclic sulfonium bromides.[9]
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References
| [7] | Meeee, M. M.; Meeeeee, M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [8] | Meeeeee, M.; Meee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [9] | Meeeeee, M.; Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) 8/8, 88.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
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