HCOOH; CH2O in neat (no solvent) Clarke-Eschweiler reductive methylation by addn. of formic acid and formaldehyde (37percent) to Sn-compd., mixt. refluxed (80°C, 24 h); cooled to room temp., standard ether-aqueous workup for an amine, elem.anal.;

1: LiAlH4 / diethyl ether 2: HCOOH; CH2O / neat (no solvent) View Scheme

1: azobisisobutyronitrile / neat (no solvent) 2: LiAlH4 / diethyl ether 3: HCOOH; CH2O / neat (no solvent) View Scheme

in tetrahydrofuran; diethyl ether addn. of tributyltin lithium soln. (prepared in situ from Li and (n-Bu)3SnCl in THF) at -7°C to soln. of the propane in dry ether, mixt.immediately turned white, stirred (2h), refluxed (1h); addn. of water, extd. with CH2Cl2, organic layer dried (MgSO4), evapn. (vac.), bulb to bulb distn. (120°C, 0.1 mmHg) of yellow liq., flash chromy. (Florisil, pentane), addn. of ethylacetate/hexane (2/5);