ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Aq. phase was extd. (ether). The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; flash chromy. (silica gel) gave 3-trimethylstannyl-3-buten-1-ol and (E)-4-trimethylstannyl-3-buten-1-ol.;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Aq. phase was extd. (ether). The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; flash chromy. on silica gel followed by distillation. (E)-1-trimethylstannyl-1-alkene not isolated, detected by gas-liq. chromy..;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne. The mixt. was stirred (6h). CH3OH, satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; The org. phase was washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; flash chromy. (silica gel) provided 3-tetrahydropyranyloxy-2-trimethylstannylpropene and (E)-3-tetrahydropyranyloxy-1-trimethylstannylpropene.;

ammonium chloride in tetrahydrofuran; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added a THF soln. of 3-tert-butyldimethylsiloxypropyne. The mixt. was stirred (6h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; The org. phase was washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; flash chromy. (silica gel) provided 3-tert-butyldimethylsiloxy-2-trimethylstannylpropene and (E)-3-tert-butyldimethylsiloxy-1-trimethylstannylpropene.;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Aq. phase was extd. (ether). The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; flash chromy. (silica gel) gave 3-trimethylstannyl-3-buten-1-ol and (E)-4-trimethylstannyl-3-buten-1-ol.;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne. The mixt. was stirred (6h). CH3OH, satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; The org. phase was washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; flash chromy. (silica gel) provided 3-tetrahydropyranyloxy-2-trimethylstannylpropene and (E)-3-tetrahydropyranyloxy-1-trimethylstannylpropene.;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Extn. of the aq. phase (ether). The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; chromy. (silica gel); distn. of the less polar oil gave 4-chloro-2-trimethylstannyl-1-butene; preparative chromy. gave minor product.;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Aq. phase was extd. with ether. The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; column chromy. (silica gel) followed by distillation. (E)-1-trimethylstannyl-1-alkene not isolated, detected by gas-liq. chromy..;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Aq. phase was extd. with ether. The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; column chromy. (silica gel) followed by distillation. (E)-1-trimethylstannyl-1-alkene not isolated, detected by gas-liq. chromy..;

ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Aq. phase was extd. (ether). The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; column chromy. (silica gel) followed by distillation. (E)-1-trimethylstannyl-1-alkene was not isolated, detected by gas-liq. chromy..;