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For use in the cleavage of ethers, see Tetra-n-butylammonium iodide, A15484.•
Catalyst for the reaction of allyltin reagents with aldehydes and ketones. Addition to the carbonyl group proceeds with allylic rearrangement: Chem. Lett., 919, 977 (1979); Acc. Chem. Res., 20, 243 (1987):
• Mild dehydration of tertiary alcohols to alkenes: Tetrahedron Lett., 32, 6489 (1991). In the Diels-Alder reaction: J. Am. Chem. Soc., 99, 8116 (1977). In THP protection of alcohols: Synthesis, 81, (1972).
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For analogous 1,4-addition to p-benzoquinones, see 2,3-Dimethoxy-5-methyl-1,4-benzoquinone, B24777.•
Reaction with ortho esters gives high yields of crystalline dialkoxycarbenium salts, useful as powerful and selective alkylating agents, (compare Triethyloxonium tetrafluoroborate, A14420 and Trimethyloxonium tetrafluoroborate, A15175): Synth. Commun., 19, 2307 (1989).• Catalyst for rearrangement of epoxides to carbonyl compounds, e.g. stilbene oxide to diphenylacetaldehyde and ring-contraction of isophorone oxide: Org. Synth. Coll., 4, 375 and 957 (1963), respectively.
• Has also been used in conjunction with BMS in the reduction of amides: J. Org. Chem., 47, 3153 (1982).
• Lewis acid catalyst in a wide variety of applications, for example:
•
Reaction with Sodium borohydride, 35788, can be used for the in situ generation of diborane. For use in the hydroboration of ɑ-pinene, see: Org. Synth. Coll., 6, 943 (1988).
有毒 (T)