Allylstannation: VI. Allylation and allenylation of aldehydes and ketones by allyl- and allenyl-tin chlorides in the presence of water

摘要: Abstract Allyl- and propargyl-carbinols can be readily prepared in one pot reaction, the presence of water, by addition allyl- or allenyl-tin chlorides to carbonyl compounds. The reactions Bu3-n(CH2CHCH2)SnCln, Bu3-n(CH3CHCHCH2)SnCln (n = 1, 2) Bu2(CH2CCH)SnCl compounds RCHO (R H, C2H5, (CH3)2CH, (CH3)3C, (E)-CH3CHCH, C6H5) RCOR′ R′ CH3 R (CH3)2CH) have been examined. monochloroorganotin derivatives undergo following quantitatvive reactions: Bu2(CH2CHCH2)SnCl + 1 2 H2O → R(HO)C(R′)CH2CHCH2 [Bu2SnCl]2O↓ (1) R(HO)C(R′)CH2CHCH (2) Reaction (2), which involves allenic substrate, is characterized rearrangement unsaturated chain, propargylic carbinol being isolated as major product (∼ 90%).