1 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