SUBSTITUTED DIETHER DIOLS BY RING-OPENING OF CARBOCYCLIC AND STANNYLENE ACETALS
作者： Rolando Martínez-Bernhardt , Peter P. Castro , Gayane Godjoian , Carlos G. Gutiérrez
DOI: 10.1016/S0040-4020(98)00563-8
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摘要: Abstract Reduction of malonaldehyde bis(ethylene and propylene acetals) with borane or monochloroborane produces diether diols 1 2 in high yield. Similar reduction glyoxal has only limited utility for the preparation tetrasubstituted triethylene glycols 3. Organotin chemistry is complementary: stannylene acetals prepared from disubstituted vicinal can be alkylated half an equivalent 1,2-dibromoethane to produce 3, two equivalents 2-chloroethanol 4.
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sci-hub.se 参考文章(57)
Stephen R. Cooper, Crown compounds : toward future applications VCH. ,(1992)
Pierre Deslongchamps, Stereoelectronic effects in organic chemistry ,(1983)
Wm.J. Considine, Organotin chemistry Journal of Organometallic Chemistry. ,vol. 5, pp. 263- 266 ,(1966) , 10.1016/S0022-328X(00)80364-2
Reed McNeil Izatt, James J. Christensen, Synthesis of Macrocycles: The Design of Selective Complexing Agents ,(1987)
Bernard Delmond, Jean-Claude Pommier, Jacques Valade, Halogénoalcoxyétains : I. (halogéno-2 alcoy)tributylétains, synthéses et propriétés. application á la préparation d'époxydes Journal of Organometallic Chemistry. ,vol. 35, pp. 91- 104 ,(1972) , 10.1016/S0022-328X(00)86886-2
George W. Gokel, Stephen H. Korzeniowski, Macrocyclic polyether syntheses ,(1982)
Clive P. Alexis, Juan M. Uribe, Jeffrey D. Beller, Gayane Godjoian, Carlos G. Gutierrez, POLYDENTATE SNXM (X = S,O,N) LIGANDS BY SELECTIVE REDUCTION OF ORGANOSULFUR HETEROCYCLES WITH TRIBUTYLTIN HYDRIDE Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 119, pp. 93- 112 ,(1996) , 10.1080/10426509608043468
George A. Olah, Takehiko Yamato, Pradeep S. Iyer, G. K. Surya Prakash, Catalysis by solid super acids. 20. Nafion-H catalyzed reductive cleavage of acetals and ketals to ethers with triethylsilane Journal of Organic Chemistry. ,vol. 51, pp. 2826- 2828 ,(1986) , 10.1021/JO00364A044
Hiroshi Ishikawa, Teruaki Mukaiyama, Reduction of Acetals with TiCl4–LiAlH4 Bulletin of the Chemical Society of Japan. ,vol. 51, pp. 2059- 2063 ,(1978) , 10.1246/BCSJ.51.2059
Deane A. Horne, Aaron Jordan, An efficient reduction of acetals and ketals to methyl ethers. Tetrahedron Letters. ,vol. 19, pp. 1357- 1358 ,(1978) , 10.1016/S0040-4039(01)94544-7