Additions to C-X &pgr;-Bonds, Part 2, Volume 2 by C.H. Heathcock

By C.H. Heathcock

Quantity 2 offers in general with the addition reactions of delocalized carbanions (enolates) and their artificial family members (metalloenamines, enol ethers, allyl organometallics) with carbonyl compounds, imines and iminium ions. significant emphasis is put on C-C bond-forming reactions similar to the aldol and Mannich reactions. Acylation reactions also are incorporated during this quantity. a number of issues that experience now not formerly been reviewed are coated, together with using enzymatic aldol reactions in synthesis and the Passerini-Ugi reactions.

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Extra resources for Additions to C-X &pgr;-Bonds, Part 2, Volume 2

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Optimized STO-3G geometry * hexagonal, * part. optimized * fully optimized * fully optimized * 3-21G geometry 230 Na--O 229 Na--N 229 Na--N 211 Na--O 211 Na--O 202 Na--F 202 Na--F 294 Na--P 294 Na--P 278 Na--S 278 Na--S 279 Na--C1 220 Na--O 210 Na--O 208 Na--O not given 51 52 74 74 86 105 144 121 172 132 169 464 441 387 141 121 19) 19) 19) 19) 19) 19) 19) 19} 19) 19) 19) 29) 29) 29) 48) 191 -v e.. o =_ -~ HC1 CH3--CN CHz--CN C,H z - N H - C H 2 L_ A ~H20-~H2 CH3--CHO CH 3 CHO CH3--NH--CH 3 CH3--NH--CH 3 HCO CH3--O--CH 3 CH3--O CH 3 O - - C H 3 CH3--O--CH 3 Na + Na* Na + Na + Na + Na ~ Na + Na + Na + Na + Na + Na + Na + Na* CH 3 NH 2 Ligand ton Table 1.

Optimized fully optimized part. optimized experimental experimental fully optimized part. optimized experimental not specified not specified experimental * part. optimized Ligand geometry/ * Complex geometry 304 C1--O 237 CI--H 345 CI--C 346 C1--C 350 C1--C 339 CI--O 331 CI--O 240 CI--H 315 C1--O 315 CI--O 331 CI--O 257 F--N R [pm] 128 91 48 50 80 49 83 88 57 50 50 378 104) 104) 107) 108) 78) 38) 44) 107) 102) 33) 106) --E(Int) Ref. - I::1 4 CH3--CN HCOOH CH3--COOH (CH3)3C--OH C6H5--NH2 C6Hs--OH CHC13 HzO H20 2 HzO 2 H20 3 HzO 4 H20 4 H20 C1- CI- C1- C1- CI- CI- C1- Br- Br- Br- Br- Br- Br Br- H, C, O CI H, C, O CI H, C, N C1 H, C, O C1 Ligand C1H O Br H O Br H O Br H O Br H O Br H O Br H O Br C1 H, C, N C1 H, C, O GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO 4-3tG 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + (4) (9/5) (14/11/5) (4/1) (9/5/1) (14/11/6) (4) (9/5) (14/11/5) (4/1) (9/5/1) (14/11/6) (4) (9/5) (14/11/5) (4) (9/5) (14/11/5) (4) (9/5) (14/11/5) [2] [4/2] [8/6/2] [2/1] [4/2/1] [8/6/3] [21 [4/2] [8/6/2] [2/1] [4/2/1] [8/6/3] [2] [4/2] [8/6/2] [2] [4/2] [8/6/21 [2] [4/2] [8/6/2] p orbital p orbital p orbital p orbital p orbital p orbital p orbital experimental * tetrahedral, * not optimized experimental * tetragonal experimental experimental * not varied experimental experimental * not varied experimental fully optimized * part.

Optimized Ligand geometry/ * Complex geometry 304 C1--O 237 CI--H 345 CI--C 346 C1--C 350 C1--C 339 CI--O 331 CI--O 240 CI--H 315 C1--O 315 CI--O 331 CI--O 257 F--N R [pm] 128 91 48 50 80 49 83 88 57 50 50 378 104) 104) 107) 108) 78) 38) 44) 107) 102) 33) 106) --E(Int) Ref. - I::1 4 CH3--CN HCOOH CH3--COOH (CH3)3C--OH C6H5--NH2 C6Hs--OH CHC13 HzO H20 2 HzO 2 H20 3 HzO 4 H20 4 H20 C1- CI- C1- C1- CI- CI- C1- Br- Br- Br- Br- Br- Br Br- H, C, O CI H, C, O CI H, C, N C1 H, C, O C1 Ligand C1H O Br H O Br H O Br H O Br H O Br H O Br H O Br C1 H, C, N C1 H, C, O GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO GTO 4-3tG 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + 4-31G 4-31G + (4) (9/5) (14/11/5) (4/1) (9/5/1) (14/11/6) (4) (9/5) (14/11/5) (4/1) (9/5/1) (14/11/6) (4) (9/5) (14/11/5) (4) (9/5) (14/11/5) (4) (9/5) (14/11/5) [2] [4/2] [8/6/2] [2/1] [4/2/1] [8/6/3] [21 [4/2] [8/6/2] [2/1] [4/2/1] [8/6/3] [2] [4/2] [8/6/2] [2] [4/2] [8/6/21 [2] [4/2] [8/6/2] p orbital p orbital p orbital p orbital p orbital p orbital p orbital experimental * tetrahedral, * not optimized experimental * tetragonal experimental experimental * not varied experimental experimental * not varied experimental fully optimized * part.

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