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Reagent/Reaction Use Ref Note DMSO/DCC (Pfitzner- Moffatt or Moffatt) Alcohol ketone/aldehyde Jacs 1963, 3027; Mech: JACS, 1965, 5561, JOC, 1967, 1926 First DMSO-based; DCC pain to remove; EDCI better DMSO/Ac2O “ Jacs 1967, 2416 DMSO/TFAA “ Jacs, 1975, 2758 DMSO/SO3-Pyridine (Parikh- Doering) “ JACS, 1967, 5505 Often under ambient conditions; best for α-chiral aldehydes/ketones (COCl)2/DMSO (swern) “ JOC, 1978, 2480; mech: Tet. 1978, 1651 Most commonly used; DMSO/Ac2O

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Oxidations at Carbon General references March, Advanced Org Chem, 1992, 1158-1238 Trost, Comp. Org. Syn. 1991, vol 7 Carey and Sundberg, Advanced Org Chem, part B, 615-664 Smith, Org Syn, Chap 3 H CH3 C(-IV) R CH3 C(-III) R CH2 OH C(-1) R CH OH RR H2 C R C(-II) R C O R C(0) R CH O C(+I) H CH2 OH C(-II) H CH O C(0) C(II) R COR O C(+III) H COH O C(+II) O C O C(+IV) RO COR O C(+IV) alkane RCH2M RCH2SiR3 RCH2X X=halide RCH2NR2 RCH2SR RCH2PR2 Acetal: RCH(OR)2

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Reactivity Umpolung-1 Ready Reactivity Umpolung: reversal of normal polarity electrophiles become nucleophiles nucleophiles become electrophiles Outline: 1. electrophilic heteroatoms 2. acyl anions 3. homoenolates 4. the cyclopropane trick 5. sulfone chemistry Normal reactivity: X x = heteroatom d = donor (Nu-) a = acceptor (E+) d a d a d X X X X or 1 3 1 5 How to make: X X or X X 1 2 1 4 complimentary

Michaely Lab publications.

1 R Co(CO)3(OC)3Co O O Δ (OC)3Co O R H O R H2 R H O (OC)4Co R (OC)4Co Co(CO)4 H H (CO)4CoH H2 CO R O H R CO (OC)3Co R (OC)3Co H R H2 R (OC)3Co R The Oxo process -developed in 1938 by Otto Roelen -Principle method for hydroformylation of terminal alkenes industrially -more that 4 million tons aldehyde annually -linear aldehydes more desirable Co2(CO)8 H2/CO (200-300 atm) 120-170 oC linear (normal) branched (iso) + chemical feed stocks linear alcohols

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Protecting Groups in Organic Synthesis-1 Ready Protecting groups are a sad fact of synthetic chemistry They are usually needed, but rarely desired Many syntheses have stalled because of trouble putting on or removing protecting groups 4 basic questions to address when choosing a P.G.: 1. Can I put it on where and only where I want? 2. Can I take it and only it off? 3. Will it survive all future reaction conditions? 4. Will it