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Int. Ed. Engl. 1987, 26 , 190 - Diasterocontrolled hydrogenation of allylic alcohols directed by the -OH group - + O K O- K+ PPh3 O PPh3 Rh H H (Ph3P)3RhCl, H2 H MeO MeO Ph Ph P Rh+ P Ph Ph Brown's Catalyst BF4- Ir + P(C 6H11)3 N PF6 - (Crabtree's Ctalyst) JACS 1983, 105 , 1072 Regioselective Hydrogenation- allylic and homoallylic alcohols are hydrogenated faster than isolated double bonds MeO2C OH MeO2C OH REDUCTIONS 33 mechanism: L + M H2 + M L L L + OH L S M L S O H lose H H H2 (oxidative addition) reductive elimination OH migratory insertion HO H L M L + H H M L S L O H Diastereoselective Hydrogenation: since -OH directs the H2, there is a possibility for control of stereochemistry - sensitive to: H2 pressure catalyst conc.

Reduction of ketones to saturated hydrocarbons H2N-NH2, KOH H O H Radical Deoxygenation Review: Tetrahedron 1983, 39 , 2609 Chem. Rev. 1989, 89, 1413. Comprehensive Organic Synthesis 1991, vol. 8, 811 Tetrahedron 1992, 48, 2529 W. B. Motherwell, D. Crich Free Radical Chain Reactions in Organic Synthesis (Academic Press: 1992) - free radical reduction of halide, thio ethers, xanthates, thionocarbanates by a radical chain mechanism. nBu3Sn-H, AIBN Ph-CH3 ↑↓ R3C-H R3C-X S X= -Cl, -Br, -I, -SPh, S S Ph , O O Barton-McCombie Reduction JCS P1 1975, 1574 R3C-X → R3C-H N N CN SMe , O CN AIBN N N X= -OC(=S)-SMe, -OC(=S)-Im, -OC(=S)Ph O O O O HO NaH, imidazole, THF, CS2, MeI O O O O O O O nBu3SnH, AIBN PhCH3, reflux O O O O (85%) O SMe S Xanthate R R Cl a) Ph nBu3SnH, AIBN PhCH3, reflux NMe2 , THF + S b) H2S, pyridine HO (73%) Ph (90%) R O Thionobenzoates S Ph O O O HO AcHN OBn N N N (CH2Cl)2 59% Ph N N N O O O O AcHN OBn S Thiocarbonyl Imidazolides nBu3SnH, AIBN PhCH3, reflux (57%) Ph O O AcHN O OBn REDUCTIONS - Cyclic Thionocarbonates: deoxygenation of 1,2- and 1,3-diols to alcohols 55 S OH N O HO MeO MeO S N O O MeO N N HO O JCS P1 1977, 1718 MeO (61%) MeO OMe nBu3SnH, AIBN PhCH3, reflux O MeO OMe OMe - Thionocarbonate Modification (Robbins) JACS 1981, 103 , 932; JACS 1983, 105 , 4059.

Crich Free Radical Chain Reactions in Organic Synthesis (Academic Press: 1992) - free radical reduction of halide, thio ethers, xanthates, thionocarbanates by a radical chain mechanism. nBu3Sn-H, AIBN Ph-CH3 ↑↓ R3C-H R3C-X S X= -Cl, -Br, -I, -SPh, S S Ph , O O Barton-McCombie Reduction JCS P1 1975, 1574 R3C-X → R3C-H N N CN SMe , O CN AIBN N N X= -OC(=S)-SMe, -OC(=S)-Im, -OC(=S)Ph O O O O HO NaH, imidazole, THF, CS2, MeI O O O O O O O nBu3SnH, AIBN PhCH3, reflux O O O O (85%) O SMe S Xanthate R R Cl a) Ph nBu3SnH, AIBN PhCH3, reflux NMe2 , THF + S b) H2S, pyridine HO (73%) Ph (90%) R O Thionobenzoates S Ph O O O HO AcHN OBn N N N (CH2Cl)2 59% Ph N N N O O O O AcHN OBn S Thiocarbonyl Imidazolides nBu3SnH, AIBN PhCH3, reflux (57%) Ph O O AcHN O OBn REDUCTIONS - Cyclic Thionocarbonates: deoxygenation of 1,2- and 1,3-diols to alcohols 55 S OH N O HO MeO MeO S N O O MeO N N HO O JCS P1 1977, 1718 MeO (61%) MeO OMe nBu3SnH, AIBN PhCH3, reflux O MeO OMe OMe - Thionocarbonate Modification (Robbins) JACS 1981, 103 , 932; JACS 1983, 105 , 4059.

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