SURVEY of 250 REACTIONS from Kurti/Czako (Ref.11)* [SIGNATURE] (Cycle Size) 2 - Acetoacetic Ester Synthesis

Home , Glaser coupling, Takai olefination

SURVEY OF 250 REACTIONS from Kurti/Czako (ref.11)* [SIGNATURE] (cycle size) 2 - Acetoacetic ester synthesis

(1) single alkylation: [HO1C 1O/HO1C 1CCX] (10) 2x

(2) double alkylation: [HO1C 1O/HO1C 1C 2CX/HC2CX] (14) 3x

4 - Acyloin Reaction [HHOC1/HHOC1CO] (10) 1x 6 - Alder ene reaction – [HC.C.CC.C] (6) 8 - Aldol reaction – (1) simple [HCC.O] (4)

(2) with dehydration [HC1C 2O 1/HC1C 2O 1] (8) 3x

10 - Alkene Metathesis [C 1C 2C 3C 4/C 1C 2C 3C 4] (8) 4x

12 - Alkyne Metathesis [C 1C 2C 3C 4/C1C 2C 3C 4/C1C 2C 3C 4] (12) 4x 14 - Amadori Rearrangement [HO.C*HC*O] (6)* 16 - Arbuzov Reaction [HP*CXCO*] (6)* 18 - Arndt-Eistert Reaction

(1) main from RCOX: [HOC1C/C 2N.NC2C 1X] (10) 2x

(2) overall from RCOOH: [NC1CCC1N.] (6)* 20 - Aza-Claisen Rearrangement [NC.C.CC.C.] (6) 22 - Aza-Cope Rearrangement [N.C.CC.C.C] (6) 24 - Aza-Wittig (Depends on input form chosen for the iminophosphorane)

(1) from R-N=PR3 [O 1C 1N 1P 1/O 1C 1N 1P 1] (8) 4x + (2) from R-NH-P R3 [HN1C 1O 1/PN1C 1O 1] (8) 3x

(3) overall from RN3 [HHO 1C 1N 1N./N1C 1O 1] (10) 26 - Aza-[2,3]-Wittig Rearrangement[HC*C.C.CN*] (6)

28 - Baeyer-Villiger Reaction [HO1CCO1H] (6)* 30 - Baker-Venkataraman [HCCO] (4) 34 - Balz-Schiemann Reaction (1) from diazonium [HFCN] (4)

(2) from amine [HFCN1N 2O 1/HN1N 2O 1/HN1N 2O] (14) 3x 36 - Bamford-Stevens-Shapiro Olefination

(1) from ketone only [HHO1C 1./CHO1C 1] (8) 2x

(2) sulfonyl-hydrazone [HN1.N 2C 1/HC.C 1N 2.N 1S] (10) 38 - Barbier Coupling Reaction [HHXCC.O] (6)

40- Bartoli Indole Synthesis – [HC1O 1N 1/HCN1O/HCCH/N 1O 1C 1.C] (16)

42 - Barton Nitrite Ester Reaction [HC1N 1X/HC1N 1.O] 44 - Barton Decarboxylation [HO.CC] (4) 46 - Barton-McCombie Deoxygenation [HHOC] (4) 48- Baylis-Hillman Reaction – [HCC.O] (4)

50 - Beckmann Rearrangement [HO1C 1.N 1/CC1O 1N ]] (8)

1 2

52 - Benzilic Acid Rearrangement [HOC*CC*.O] (6) 54 - Benzoin Condensation [HCC.O] (4) 56 - Bergman Cycloaromatization [HHC.CC.C] (6)

58 - Biginelli Reaction [HN1C 1H/HN1C 1O 1/HNC2O 2/HC3.C 2O 2/HC3C 1O 1] (20) 60 - Birch Reduction [HHC.C.C.C] (6)

62 - Bischler-Napieralsky Isoquinoline Synthesis [HNC1O 1/HCC1O 1] (8) 2x 64 - Brook Rearrangement [HO*SiC*] (4) 66- Brown Hydroboration [HBC.C] (4)

68 - Buchner Ring Expansion [NC1CCC1N.] (6)* 70 - Buchwald-Hartwig Cross-coupling [HNCX] or [HOCX] (4) 72 - Burgess (Chugaev) Dehydration [HC.CO] (4) 74 - Cannizzaro Reaction (1) two products [HOCHC.O] (6) (2) ester product [HC.OC] (4) 76 - Carroll Rearrangement [OC.C.CCC.] (6) 78 - Castro-Stevens Coupling [HOC.CCX] or [HNC.CCX] (6) 80 - Chichibabin Oxidative Amination [HNCH] (4)

82 - Ciammician-Dennstedt Rearrangement [HN.C1C 2C 3X/HC3C 2C 1C 3X] (12) 3x 86 - Claisen Condensation [HCCO] (4) 88 - Claisen Rearrangement [OC.C.CC.C.] (6) 90 -Claisen-Ireland Rearrangement [HCC.C.CO] (6)

92 - Clemmensen Reduction [HHO1C 1/HHO 1C 1] (8)

94 - Combes Quinoline Synthesis [HN1C 1O 1/HN1C 1O 1/HC.C2O 2/HCC2O 2] (16) 96 - Cope Elimination (1) from amine oxide [HC.CN] (4) (2) overall from amine [HONC.CH] (6) 98 - Cope Rearrangement [CC.C.CC.C.] (6) 100 - Cope-Ireland Rearrangement [HCC.C.CC] (6) 102 - Corey-Chaykovsky

(1) epoxidation [HC1O.CC1S] (6)*

(2) cyclopropanation [HC1C.CC1S] (6)*

104 - Corey-Fuchs Alkyne Synthesis [HHXC1/HHXC1C 2H/XC1C 2O 1/HHXC1C 2O 1] (20) 104 - Corey-Bakshi-Shibata Reduction [HHO.C] (4) 106 - Corey-Kim Oxidation [HO.CH] (4) 108 - Corey-Nicolaou Macrolactonization [HOCO] (4) 110 - Corey-Winter Olefination [HHOC.CO] (6) 112 - Cornforth Rearrangement [OCO.C.C.C.] (6) 114 - Criegee Oxidation [HO.CC.OH] (6)

------Criegee Ozonolysis (not shown) [HO1C 1C 2O 2H/HO1C 1C 2O 2H] (12) 4x

2 3

116 - Curtius Rearrangement

(1) R-COOH + HX  R-COX + H2O [HXCO] (4)

(2) R-COX + HN3  R-CON3 + HX [HNCX] (4)

(3) R-CON3  R-NCO + CO2 [N1N.NN1.CC] (6)*

(4) R-NCO + H2O  R-NH2 + CO2 [HO1C 1N 1/HO1C 1N 1] (8) 3x

(5) R-COX + HN3  R-NCO + N 2 + HX[HN1C 1C/N 1N.NN1C 1X] (10)

overall: R-COOH + HN3  RNH2 + CO2+N2 [HO.CC/N 1N.NN1] (8) 1x 118 - Dakin Oxidation [HOCCOH] (6) 120 - Dakin-West Reaction [HO.CCCO] (6)

122 - Dannheiser Benzannulation [HC1C 2.C 3/C 4C 1C 2.C 3C 4.O] (10) 4x 124 - Dannheiser Cyclopentene Annulation [SiCC.CC.C] (6) 126 - Danishefsky Diene – 126 (1) simple Diels-Alder: [C.C.C.CC.C] (6) (2) to ketone product [HOSiO/C.CC.CC.C] (10) (3) with alkyne to phenol [HOSiO/HCCC.CCO] (10) (4) with ketones [O.CC.C.C.O] (6) 128 - Darzens Reaction

(1) to epoxy ester [HC1O.CC1X] (6)*

(2) to aldehyde (-CO2) [HO1C 1O/HO1C 1C 2/O 2C 3C 2H/C 3O 2C 2X] (16) 130 - Davis Oxaziridine

(1) Formation [HO1N.CO1H] (6)*

(2) Oxidation [HCO1N.CO1] (6)* 132 - DeMayo Cycloaddition (1) direct [C.CC.C] (4) (2) to 1,5-diketone [C.CCC] (4) 134 - Demjanov (and Tiffeneau) Rearrangement

(without specified HNO2) [HOC*CC*N] (6) 136 - Dess-Martin Oxidation [HOCH] (4) 138 - Dieckmann Condensation [HCCO] (4)

138 - Thorpe-Ziegler Cyclization [HC1C 2N 1/HC1C 2N 1] (8) 3x 140 - Diels-Alder Cycloaddition [C.C.C.CC.C] (6) 142 -Dienone-phenol Rearrangement [HC*CC*.C.C.C.O] (8)

144 - Dimroth Rearrangement [HN1.C 1.N 2/HN1C 2N 2] (8)

146 - Doering Allene Synthesis [HHXC1/C2C 3C 1HXC1/C 2C 3C 1X] (14) 148 - Dotz Benzannulation

[HC1C6C.CC3C2H/XCO.C3C2.C1C6.O] (16) AMBIV = 2 C 150 - Enders Hydrazone Alkylation (net from ketone) [HCCX] (4)

152 - Enyne Metathesis – [C 1C 2C 3C 4/C 1C 2C 3C 4] (8) 4x

154 - Eschenmoser Methenylation [HC1C 2N 1/HC1C 2N 1CX] (10) 3x

156 - Eschenmoser-Claisen [HO1C 1O/HCC.C.CO1C 1O] (12) 2x

158 - Eschenmoser-Tanabe [HN1.N2C 1.C 2O./CC2.C1N 2.N1S] (12) 3 4

160 - Eschweiler-Clarke Methylation [HHO 1C 1/NHO1C 1] (8) 2x 162 - Evans Aldol [HCC.O] (4) 164 - Favorsky Rearrangement [HOC*CC*X] (6)

166 - Feist-Benary Furan Synthesis [HC1C 2H/XC2.C3O 1/HC1.C.OC3O 1] (14) 4x 168 - Ferrier Reaction [HZC.C.CO] (6) (for Z = O, S, N, C)

Ferrier Rearrangement [HOC1O./C.CC1O] (8) 1x 170 - Finkelstein Reaction [HXCX’] (4)

172 - Fischer Indole Synthesis [HCC1H/N 1NC2N 1/HC1.C 2N 1] (12) 3x

174 - Fleming Oxidation [HO1CSiO1H] (6)• 176 - Friedel-Crafts Acylation [HCCO] (4) 178 - Alkylation [HCCX] (4) 180 - Fries Rearrangement [HC*CO*] (4) 182 - Gabriel Synthesis [HNCX] (4) 184 - Gattermann Formylation (1) with :CO [HCC] (3) AMBIV = C

(2) with HCN [HO1C 1N 1/HO1C 1N 1/HCC 1N 1] (12) 3x 186 – Glaser Coupling [HCCH] (4) 188 – Grignard Reaction (1) H = MgX [HCC.O] (4) (2) just by redn of R-X [HHXCC.O] (6) 190 – Grob Fragmentation [HO.CC.CX] (6)

192 – Hajos-Parrish Reaction [HC1C 2O 1/HC1C 2O 1/HCC.C] (12) 3x 194 – Hantzsch DihydroPyridine Synthesis (4-component)

[HN1C 1O 1/HN1C 5O 2/HC4.C 5O 2/HC4C 3O 3/HC2C 3O 3/HC2.C 1O 1] (24) 9x Hantzsch Pyridine Synthesis (4-component + oxidation)

[HN1C 1O 1/HC2C 3H/HN1C 5O 5/HN1C 5O 5/HC4C 3O 3/HC4C 3O 3/HC2.C 1O 1] (28) 9x

Hantzsch Pyrrol Synthesis [HNC1.O1/HCC2H/XC2.C1O 1] (12) 3x 196 – Heck Reaction [HCCX] (4) 198 – Heine Reaction [O.C.NC] (4) 200 – Hell-Volhardt-Zelinsky Reaction [HXCH] (4) 202 – Henry Reaction - (A) one step [HCC.O] (4)

(B)+ dehydration [HC1C 2O 1/HC1.C2O 1] (8) 3x

204 – Hetero Diels-Alder [A.B.C.DE.F] (6) - with many possible heteroatom choices (18 common ones in rev.11) 206 – Hofmann Elimination [HC.CNCX] (6) 208 – Hofmann-Loffler-Freytag Reaction [HNCX] or [HNCH] (4) 210 – Hofmann Rearrangement

(1) RCOOH  RCONH2 [HNCO] (4)

(2) RCONH2  RNCO [HN1.CCN1H] (6) 3,3 4 5

(3) R-NCO + H2O  R-NH2 + CO2 [HO1C 1N 1/HO1C 1N 1] (8) 3x

(4) R-CONH2 + H2O  R-NH2 + CO2 [HO1C 1N/CC1O 1H] (8) 2x

overall: R-COOH + NH3  R-NH2 + CO2 [HO.CCNH] (6} 212 –Horner-Wadsworth-Emmons Olefination

(214 also) [HC1C 2O 1/PC1C 2O 1] (8) 3x

216 – Houben-Hoesch Reaction - [HO1C 1N 1/HO1C 1N 1/HCC1N 1] (12) 3x 218 – Hunsdiecker Reaction [HXCC.OH] (6) ------Isocyanate Cycloaddition [N.CC.C] (4) 220 – Jacobsen Reaction [HOCO] (4)

222 – Jacobsen Enantioselective Epoxidation [HO1C.CO1H] (6)*

224 – Japp-Klingemann Reaction [HOCC1N 1.N2/HC1N 1.N2] (10) 3x

226 – Johnson-Claisen Rearrangement [HO1C 1O/HCC.C.CO1C 1O] (12) 2x 228 – Jones Oxidation [HO.CH] 230 – Julia Lythgoe Olefination

(1) external reduction [HHO1C 1C 2S/HC 2C 1O 1] (10)

(2) internal reduction/ambivalent S [HC1C 2O 1/CSC 1C 2O 1] (9) AMBIV = S 232 – Kagan-Samarium Reduction [HHXCC.O] (6)

double construction [HHXCC1.O/HHXCC1O] (12) 1x 234 – Kahne Glycosidation [HOCO] (4) 236 – Keck Allylation [SnC.C.CC.O] (6) 238 – Keck Macrolactonization [HOCO] (4) 240 – Keck Allylation [SnC.C.CCX] (6)

242 – Knoevenagel Condensation [HC1C 2O 1/HC1C 2O 1] (8) 3x

244 – Knorr Pyrrole Synthesis [HNC1O 1/HC2C 3O 2/HC.C3O 2/HC2.C1O 1] (16) 5x 246 – Koenigs-Knorr Glycosidation [HOCX] (4) 248 – Kolbe-Schmitt Reaction [HCC.O] (4)

250 – Kornblum Oxidation [HO1C 1H/HO1C 1X] (8) 2x 252 – Krapcho Reaction [HXCO.CC] or [HCCO.CC] (6) 254 – Krohnke Pyridine Synthesis

[HN1C 1O 1/HN1C 5O 2/HN1C 5O 2/HC 2C 3H/O1C 1.C2X] (20) 6x 256 – Kulinkovich Reaction

(1) Grignard to ester/amide [HCC1O 1/HCC1O 1] (8) 2x

(2) From alkene [HHO1C 1/C.CC1O 1] (8) (323) 258 – Kumada Cross-coupling [HCCX] (4) 260 – Larock Indole Synthesis [HNC.CCX] (6) 262 – Ley Oxidation [HO.CH] (4)

264 – Lieben Haloform Reaction [HXC1H/HXC1H/HXC1COH] (14) 1x 266 – Lossen Rearrangement

(1) R-COOH  R-CONHOH+H2O [HNCO] (4)

(2) R-CONHOH  R-NCO + H2O [HN1.CCN1O] (6)*

(3) R-NCO+H2O  R-NH2 + CO2 [HO1C 1N 1/HO1C 1N 1] (8) 3x

5 6

(4) R-CONHOH  R-NH2 + CO2 [HO1C 1N 1/CC1O 1N ]] (8) 3x-B

overall R-COOH + NH2OH  RNH2 + CO2 + H2O [HO1C 1C/NO1C 1O] (8) 2x 268 – Luche Reduction [HHO.C] (4)

270 – Madelung Indole Synthesis [HC1C 2O 1/HC1C 2O 1] (8) 3x 272 – Malonic Ester Synthesis

(1) single alkylation [HO1C 1O/HO1C 1CCX] (10) 2x

(2) double alkylation [HO1C 1O/HO1C 1C 2CX/HC2CX] (14) 3x

274 – Mannich Reaction [HNC1O 1/HCC1O 1] (8) 2x

276 – McMurry Coupling [HHO1C 1C 2O 2/HHO1C 1C 2O 2] (12) 4x 278 – Meerwein Arylation [HCCN] (4) 280 – Meerwein-Ponndorf-Verley Redn [HHO.C] (4) 282 – Meisenheimer Rearrangement [HO*CN*] (4)

284 – Meyer-Schuster Rearrangement [HO1C 1.C2./CO1C 1.C2] (8) 3x

284 – Rupe Rearrangement [HO1C 1.C 2/HC.CO1C1.C 2] (10) 3x 286 – Michael Reaction [HCC.C] or [HNC.C] or [HOC.C] (4) 288 – Midland Alpine Borane Redn [HHO.C] (4) 290 – Minisci Reaction [HCCX] (4) 292 – Mislow-Evans Rearrangement [OSC.C.C] (5) AMBIV = S 294 – Mitsunobu Reaction [HZCO] (4) (Z = O,S,N,C) 296 – Miyaura Boration [XCBB] (4) 298 – Mukaiyama Aldol Reaction [SiOC.CC.O] (6) 300 – Myers Asymmetric Alkylation [HCCX] (4) 302 – Nagata Hydrocyanation [HCC.C] (4) 304 – Nazarov cyclization [HCC.C] (4) 306 – Neber Rearrangement

from oxime [HO1C 1N 1/HCN1O 1C 1N 1] (10) 3x from ketone [HCNO] (4)

308 – Nef Reaction [HO1C 1H/N1O 1C 1N 1] (8) 3x 310 – Negishi Cross-coupling [HHXCCX] (6)

312 – Nenitzescu Indole Synthesis [HNC1O 1/HCC2H/O.C.C.C2.C1.O1] (14) 2x 314 – Nicholas Reaction [HCCX] or [HNCO] (4) 316 – Noyori Hydrogenation [HHC.C] (4) 318 – Nozaki-Hiyama-Kishi Reaction [HHXCC.O] (6) 320 – Oppenhauer Oxidation [HO.CH] (4) 322 – Overman Rearrangement [OC.C.CN.C] (6) 324 – Oxy-Cope Rearrangement [HO.C*C.C.CC.C*] (8)

326 – Paal-Knorr Furan Synthesis [HC.C1O 1/HC.C.OC1O 1] (10) 2x

328 - Paal-Knorr pyrrole Synthesis [HN1C 1O/HN1C 2O/HC.C1O/HC.C2O] (16) 5x 330 – Passerini Reaction

(1) + H2O (or RCOOH) [HOC1O 1/C2HN1.C2/O 1C 1C 2.N 1] (12)

(2) + HN3 [HNC2H/N1C 2NN/N1C 2C 1O] (12) 6 7

332 – Paterno-Buchi Reaction [O.CC.C] (4) 334 – Pauson-Khand Reaction [C.CCC.C] (5) AMBIV = C 336 – Payne Rearrangement [HOCO] (4)

338 – Perkin Reaction [HC1C 2O 1/HC1C 2O 1CO] (10) 3x

340 – Petasis Boronic Mannich Reaction [HNC1O 1/BCC1O 1] (8) 2x

342 – Petasis-Ferrier Rearrangement [Ti1C 1CO1/ Ti1C 1CO1] (8)

344 – Peterson Olefination [HC1C 2O 1/SiC1C 2O 1] (8) 3x 346 – Pfitzer-Moffat Oxidation [HO.CH] (4)

348 – Pictet-Spengler Reaction [HNC1O 1/HCC1O 1] (8) 2x 350 – Pinacol Rearrangement [HO.C*CC*O] (6) 352 – Pinner Reaction [HOC.N] or [HNC.N] (4) 354 – Pinnick Oxidation [HOCH] (4)

356 – Polonovski Reaction [HO1C 1H/XCN1O 1C 1N 1] (10) 3x

358 – Pomerantz-Fritsch Reaction [HN1C 1O 1/HN1C 1O 1/HC.C2O/HCC2O] (6) 360 – Prevost Reaction [HOC.COH] (6)

362 – Prilezhaev Epoxidation [HO1C.CO1H] (6)* 364 – Prins Reaction (A) [HCC.O] (4) (B) [HOC.CC.O] (6) (C) [O.CO.CC.C] (6) 366 – Prins-Pinacol Rearrangement [HO.C*C/C*.CCO/HOCO] (12) 3x4 368 – Pummerer Rearrangement [HCOSOCS] (7) AMBIV = S 370 – Quasi-Favorsky = Favorsky [HOC*CC*X] (6) 372 – Ramberg-Backlund Reaction [HCCSCCX] (7) AMBIV = S 374 - Reformatsky Reaction [HHXCC.O] (6)

376 – Regitz Diazo Transfer [HC1N 1.N2/HC1N 1.N 2] (8) 3x

378 – Reimer-Tiemann Reaction [HO1C 1X/HO1C 1X/HCC1X] (12) 2x

380 - Riley SeO2 Oxidation [HO1C 1H/HO1C 1H] (8) 2x

382 – Ritter Reaction (CN + C=C) [HO1C 1H/XCN1O 1C 1N 1] (10) 3x

(CN + C-OH) [HO1C 1.N1/CO1C 1.N1] (8) 3x

384 – Robinson Annelation [HC1C 2O 1/HC1C 2O 1/HCC.C] (12) 3x 386 – Roush Allylation [HOBC./C.CC.O] (8) 388 – Rubottom Oxidation [HOCH] (4) 390 – Saegusa Oxidation [HC.C.C.OSi] (6) 392 – Sakurai Allylation [HOSiC./C.CC.O] (8) 394 – Sandmeyer Reaction [HXCN] or [HCCN] (4) 396 – Schmidt Reaction

(A) RCOOH + HN3 [HO.CC/N1N.NN1] (8) 1x

(B) RCHO + HN3 [HN1C 1O 1/HC1N 1N./NN1C 1O 1] (12) 3x 398 – Schotten-Baumann Reaction [HNCX] or [HOCX] (4)

7 8

400 – Schwartz Hydrozirconation [HZrC.C] (4)

402 – Seyferth-Gilbert Homologation [HC1C 2O 1/PC1C 2C/C1N.NC1C 2O 1] (14) 3x 404 – Sharpless Aminohydroxylation [HOC.CNH] (6) 406 – Sharpless dihydroxylation [HOC.COH] (6)

408 – Sharpless epoxidation [HO1C.CO1H] (6)*

410 – Shi epoxidation [HO1C.CO1H] (6)* 414 - Skraup Quinoline Synthesis

(A) (oxidn: ΔH=-2) [HN1C 1H/OC1N 1H/OC.C2H/OC2CH] (16) 3x

(B) (not redox) [HN1C 1H/HN1C 1.C.C2O 1/HCC2O 1] (14) 4x 416 – Smiles Rearrangement [HOCS] (4); MANY (4x4=16: [HZCZ’])

418 - Smith-Tietze Coupling (= 2x Brook-64) [HOSiC1CO/HC1CO] (10) 1x 420 – Snieckus Ortho metalation (A) [HCCX] (4) (B) [HCC.O] (4) 422 – Sommelet-Hauser Rearrangement [HCC*HN*C] (6) 424 – Sonogashira Cross-coupling [HCCZ] (4) 426 – Staudinger Ketene [O.CC.C] or [ N.CC.C] (4)

428 – Staudinger Reaction (1) [HOPH/N1N.NN1] (8) 1x (2) - overall [HNCX] (4)

430 – Stephen Reduction [HHC1N 1/HO1C 1N 1/HO1C 1N 1] (12) 3x 432 – Stetter Reaction [HCC.C] (4) 434 – Stevens Rearrangement [HC*CN*] (4) [HC*CS*] (4\) 436 – Stille Carbonyl Cross-coupling [SnCCCX] (5) AMBIV = C (:CO) 438 – Stille Cross-coupling [SnCCX] (4) 440 – Stille-Kelly Coupling [HHXCCX] (6)

442 – Stobbe Condensation [HC1C 2O 1/HC1C 2O 1CO] (10) 3x 444 – Stork Enamine Synthesis [HCCX] (4)

446 – Strecker Reaction [HOC1H/N1C 1O 1C 2/N1C 1O 1C 2C 1N 1] (14) 4x 448 – Suzuki Coupling [BCCX] (4) 450 - Swern Oxidation [HO.CH] (4)

452 – Takai Olefination [HHXC1C 2O 1/HHXC1C 2O 1] (12) 3x

454 – Tebbe Olefination [HC1C 2O 1/Ti1C 1C 2O 1Ti1C] (10) 4x 456 – Tishchenko Reaction (A) [HCO.C] (4) (B) [HOCHC.O] (6) 458 - Tsuji-Trost Allylation [HCC.C.CX] (6) 460 – Tsuji-Wilkinson [CCC] (3) AMBIV = C (:CO) 462 – Ugi Multicomponent Reactions = 5 types of product

(1) - no added H2O [HNC1O 1/C 2HN1.C 2/O 1C 1C 2.N 1] (12) 4x

(2) + RCOOH [HN1C 1O 1/C2HO2C/N1HN2.C2/O1C 1C 2.N2] (16) 4x

(3) + CO2+ROH [HOC1O 1/HN1C 2O 2/C3HO1C 1/N1HN2.C3/O2C 2C 3.N2] (20) 7x

(4) + HNCO [HN1C 1O 1/HN1C.NC2H/O 1C 1C 2.N] (14) 4x

8 9

(5) + HN3 (cyclic) [HNC1O 1/HN1C 2H/O1C 1C 2.N2/NN1C 2.N2] (16) 4x 464 – Ullmann Biaryl-ether Synthesis [HOCX] (4) 466 – Ullmann Reaction [HHXCCX] (6) 468 – Vilsmeier Formylation [HCCN] (4) 470 – Vinyl-cyclopropane Rearrangement [C.C.CC] (4)

472 – von Pechmann Reaction [HOCO/HC.C1O 1/HCC1O 1] (12) 2x

474 – Wacker Oxidation [HO1C 1H/HO1C 1.C] (8) 2x 476 – Wagner-Meerwein Rearrangements (A) [HC*CC*] or [XC*CC*] (4) (B) [HOC*CC*X] (6)

482 – Wharton Olefin Synthesis [HH01C 1./C.CO1C 1] (8) 2x 484 – Williamson Ether Synthesis [HOCX] (4) 486 – Wittig Reaction + (1) From P R3 [HC1C 2O 1/PC1C 2O 1] (8) 3x

(2) from RSP=C + C=O [HC1C 2O 1/PC1C 2O 1] (8) 4x

(3) overall from CHX+C=O [HHXC1C 2O 1/HC1C 2O 1] (10) 3x

488 - Wittig-Schlosser Reaction [HC1C 2O 1/PC1C 2O 1] (8) 3x 490 – Wittig Rearrangements (1,2) [HC*CO*] (4) (1,3) [HC*C.C.CO*] (6) 492 – Wohl-Siegler Bromination [HCXN] (4) or [HC.C.CXN] (6) 494 – Wolff Rearrangement

(1) main from RCOX: [HOC1C/C 2N.NC2C 1X] (10) 2x

(2) overall from RCOOH: [NC1CCC1N.] (6)*

496 – Wolff-Kishner Reduction [HHO1C 1/HHO 1C 1] (8) 2x

or with N2 = [HN1.N2HO1C 1/HN1.N2HO1C 1] (12) 4x 498 – Wurtz Coupling [HHXCCX] (6) 500 – Yamaguchi Macrolactonization [HOCO] (4) ------

* The reactions are ordered alphabetically and by page, as in ref. 11. The signatures in brackets are modified by a star (*) for 6-cycle reactions with only one atom doubly exchanging, and by the form (1x, 2x, 3x, 4x) for 8, 10, and 12-cycle reactions. Rearrangement titles are underlined.