Tetrahedron p. 8919 - 8932 (1998)
Update date:2022-08-30
Topics:
Martinez-Bernhardt, Rolando
Castro, Peter P.
Godjoian, Gayane
Gutierrez, Carlos G.
Reduction of malonaldehyde bis(ethylene and propylene acetals) with borane or monochloroborane produces diether diols 1 and 2 in high yield. Similar reduction of glyoxal his(ethylene acetals) has only limited utility for the preparation of tetrasubstituted triethylene glycols 3. Organotin chemistry is complementary: stannylene acetals prepared from disubstituted vicinal diols can be alkylated with half an equivalent of 1,2-dibromoethane to produce tetrasubstituted triethylene glycols 3, or with two equivalents of 2-chloroethanol to produce disubstituted triethylene glycols 4.
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