1

OSR 15 アルケンとアルキンへの付加反応

目次： プロトン化から始まる反応 ハロゲン化水素の付加 H2Oと ROHの酸触媒付加 RCO2Hの付加 オキシ水銀化 ヒドロ水素化－酸化 ハロゲン化 臭素化 塩素化 共役ジエンへの求電子付加 エポキシ化 シクロプロパン化（カルベン付加） Diels–Alder反応 オゾン分解 ジヒドロキシル化 水素化

プロトン化から始まる反応 ハロゲン化水素の付加

(Reaction without solvent) R.A. Pacaud, C.F.H. Allen, Org. Synth., Coll. Vol. 2, 336 (1943).

H. Stone, H. Shechter, Org. Synth., Coll. Vol. 4, 543 (1963).

H2Oと ROHの酸触媒付加

G.F. Woods, Org. Synth., Coll. Vol. 3, 470 (1955).

2

R.A. Earl, L.B. Townsend, Org. Synth., Coll. Vol. 7, 334 (1990).

R.E. Ireland, T.H. O'Neil, G.L. Tolman, Org. Synth., Coll. Vol. 7, 66 (1990).

F.P. Tise, P.J. Kropp, Org. Synth., Coll. Vol. 7, 304 (1990).

F. Loiseau, A.M. Beauchemin, Org. Synth., 90 , 87 (2013).

RCO2Hの付加

A.L. McCloskey, G.S. Fonken, R.W. Kluiber, W.S. Johnson, C. Raha,

Org. Synth., Coll. Vol. 4, 261(1963).

3

D.C. Kleinfelter, P. von R. Schleyer, Org. Synth., Coll. Vol. 5, 852 (1973).

J. Meinwald, J. Crandall, W.E. Hymans, Org. Synth., Coll. Vol. 5, 863 (1973).

オキシ水銀化

J.M. Jerkunica, T.G. Traylor, Org. Synth., Coll. Vol. 6, 766 (1988).

H.E. Carter, H.D. West, Org. Synth., Coll. Vol. 3, 774 (1955).

G.W. Stacy, R.A. Mikulec, Org. Synth., Coll. Vol. 4, 13 (1963).

M.S. Newman, W.R. Reichle, Org. Synth., Coll. Vol. 5, 1024 (1973).

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ヒドロ水素化－酸化

(“Disiamylborane” is used as a highly selective sterically hindered borane.)

H. Kono, J. Hooz, Org. Synth., Coll. Vol. 6, 919 (1988).

G.W. Kabalka, J.T. Maddox, T. Shoup, K.R. Bowers,

Org. Synth., Coll. Vol. 9, 522 (1998).

J.J. Partridge, N.K. Chadha, M.R. Uskokovoc, Org. Synth., Coll. Vol. 7, 339 (1990).

(The reagent here is the sterically hindered disiamylborane obtained as above.)

E.M. Kaiser, R.A. Benkeser, Org. Synth., Coll. Vol. 6, 852 (1988).

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E.J. Leopold, Org. Synth., Coll. Vol. 7, 258 (1990).

ハロゲン化 臭素化

J.R. Johnson, W.L. McEwen, Org. Synth., Coll. Vol. 1, 521 (1941).

H.R. Snyder, L.A. Brooks, Org. Synth., Coll. Vol. 2, 171 (1943).

H.S. Rhinesmith, Org. Synth., Coll. Vol. 2, 177 (1943).

T.W. Abbott, D. Althousen, Org. Synth., Coll. Vol. 2, 270 (1943).

N.H. Cromwell, R. Benson, Org. Synth., Coll. Vol. 3, 105 (1955).

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S.M. McElvain, D. Kundiger, Org. Synth., Coll. Vol. 3, 123 (1955).

P.Z. Bedoukian, Org. Synth., Coll. Vol. 3, 127 (1955).

(Electrophilic bromination in homogeneous solution.)

A.W. Langman, D.R. Dalton, Org. Synth., Coll. Vol. 6, 184 (1988).

L.F. Fieser, Org. Synth., Coll. Vol. 4, 195 (1963).

L.I. Smith, M.M. Falkof, Org. Synth., Coll. Vol. 3, 350 (1955).

H. Adkins, R.E. Burks, Jr, Org. Synth., Coll. Vol. 3, 785 (1955).

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N.A. Khan, F.E. Deatherage, J.B. Brown, Org. Synth., Coll. Vol. 4, 851 (1963).

N.A. Khan, Org. Synth., Coll. Vol. 4, 969 (1963).

R.C. Fuson, J.W. Kneisley, E.W. Kaiser, Org. Synth., Coll. Vol. 3, 209 (1955).

S.I. Ngi, E. Anselmi, M. Abarbri, S. Langle, A. Duchêne, J. Thibonnet,

Org. Synth., 85 , 231 (2008).

塩素化

R. Paul, O. Riobé, M. Maumy, Org. Synth., Coll. Vol. 6, 675 (1988).

W. Weyler, Jr, W.G. Duncan, M.B. Liewen, H.W. Moore, Org. Synth., Coll. Vol. 6, 210 (1988).

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G.H. Coleman, H.F. Johnstone, Org. Synth., Coll. Vol. 1, 158 (1941).

H.B. Donahoe, C.A. Vanderwerf, Org. Synth., Coll. Vol. 4, 157 (1963).

G.A. Ropp, W.E. Creig, V. Raaen, Org. Synth., Coll. Vol. 4, 130 (1963).

共役ジエンへの求電子付加

R.B. Moffett, Org. Synth., Coll. Vol. 4, 238 (1963).

エポキシ化

H. Hibbert, P. Burt, Org. Synth., Coll. Vol. 1, 494 (1941).

D.J. Reif, H.O. House, Org. Synth., Coll. Vol. 4, 860 (1963).

J.R. Salaun, J. Champion, J.M. Conia, Org. Synth., Coll. Vol. 6, 320 (1988).

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M. Korach, D.R. Nielsen, W.H. Rideout, Org. Synth., Coll. Vol. 5, 414 (1973).

R.L. Wasson, H.O. House, Org. Synth., Coll. Vol. 4, 552 (1963).

D. Felix, C. Wintner, A. Eschenmoser, Org. Synth., Coll. Vol. 6, 679 (1988).

W.J. Linn, Org. Synth., Coll. Vol. 5, 1007 (1973).

R.D. Bach, J.W. Knight, Org. Synth., Coll. Vol. 7, 126 (1990).

J.-P. Bégué, D. Bonnet-Delpon, A. Kornilov, Org. Synth., Coll. Vol. 10, 703 (2004).

A. Roebuck, H. Adkins, Org. Synth., Coll. Vol. 3, 217 (1955).

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L.A. Paquette, J.H. Barrett, Org. Synth., Coll. Vol. 5, 467 (1973).

E. Vogel, W. Klug, A. Breuer, Org. Synth., Coll. Vol. 6, 862 (1988).

シクロプロパン化（カルベン付加）

R.D. Smith, H.E. Simmons, Org. Synth., Coll. Vol. 5, 855 (1973).

Y. Ito, S. Fujii, M. Nakatuska, F. Kawamoto, T. Saegusa,

Org. Synth., Coll. Vol. 6, 327 (1988).

O.H. Kvernenes, L.K. Sydnes, Org. Synth., Coll. Vol. 11 , 586 (2009).

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E. Vogel, W. Klug, A. Breuer, Org. Synth., Coll. Vol. 6, 731 (1988).

K.R. Mondanaro and W.P. Dailey, Org. Synth., Coll. Vol. 10, 658 (2004).

K. Maruoka, S. Sakane, H. Yamamoto, Org. Synth., Coll. Vol. 8, 321 (1993).

M.N. Mattson, E.J. O'Connor, P. Helquist, Org. Synth., Coll. Vol. 9, 372 (1993).

H.-U. Reissig, I. Reichelt, T. Kunz, Org. Synth., Coll. Vol. 9, 573 (1993).

A.B. Charette, H. Lebel, Org. Synth., Coll. Vol. 10, 613 (2004).

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M.E. Scott, N.-W. Tseng, M. Lautens, Org. Synth., 85, 172 (2008).

Diels–Alder反応

A.C. Cope, E.C. Herrick, Org. Synth., Coll. Vol. 4, 890 (1963).

S. Danishefsky, T. Kitahara, P.F. Schuda, Org. Synth., Coll. Vol. 7, 312 (1990).

C.F.H. Allen, A. Bell, Org. Synth., Coll. Vol. 3, 310 (1955).

M. Oda, T. Kawase, T. Okada, T. Enomoto, Org. Synth., Coll. Vol. 9, 186 (1998).

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R. Rathore, C.L. Burns, M.I. Deselnicu, Org. Synth., Coll. Vol. 11 , 62 (2009).

M.E. Jung, C.A.McCombs, Org. Synth., Coll. Vol. 6, 445 (1988).

S.A. Kozmin, S. He, V.H. Rawal, Org. Synth., Coll. Vol. 10, 442 (2004).

P.G. Gassman, K.T. Mansfield, Org. Synth., Coll. Vol. 5, 96 (1973).

P.G. Gassman, J.L. Marshall, Org. Synth., Coll. Vol. 5, 424 (1973).

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K.-H. Scholz, H.-G. Heine, W. Hartmann, Org. Synth., Coll. Vol. 7, 4 (1990).

P. Binger, P. Wedemann, U.H. Brinker, Org. Synth., Coll. Vol. 10, 231 (2004).

M. Korach, D.R. Nielsen, W.H. Rideout, Org. Synth., Coll. Vol. 5, 414 (1973).

V. Singh, M. Porinchu, P. Vedantham, P.K. Sahu, Org. Synth., Coll. Vol. 11, 514 (2009).

L.F. Fieser, Org. Synth., Coll. Vol. 5, 604 (1973).

D.L. Boger, M.D. Mullican, Org. Synth., Coll. Vol. 8, 444 (1993).

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R. Pettit, J. Henery, Org. Synth., Coll. Vol. 6, 422 (1988).

H. Hopf, I. Böhm, J. Kleinschroth, Org. Synth., Coll. Vol. 7, 485 (1990).

R.I. Longley, Jr., W.S. Emerson, A.J. Blardinelli, Org. Synth., Coll. Vol. 4, 311 (1963).

K.R. Dahnke, L.A. Paquette, Org. Synth., Coll. Vol. 9, 396 (1998).

D. Spitzner, A. Engler, Org. Synth., Coll. Vol. 8, 219 (1993).

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A. Padwa, M.A. Brodney, S.M. Lynch, Org. Synth., Coll. Vol. 10, 188 (2004).

D.L. Boger, J.S. Panek, M. Yasuda, Org. Synth., Coll. Vol. 8, 597 (1993).

S. Pikul, E.J. Corey, Org. Synth., Coll. Vol. 9, 67 (1998).

オゾン分解

L.F. Tietze, M. Bratz, Org. Synth., Coll. Vol. 9, 314 (1998).

A.R. Van Dyke, K.M. Miller, T.F. Jamison, Org. Synth., Coll. Vol. 11, 205 (2009).

17

R.E. Claus, S.L. Schreiber, Org. Synth., Coll. Vol. 7, 168 (1990).

F.F. Fleming, B.C. Shook, Org. Synth., Coll. Vol. 10, 591 (2004).

P.S. Bailey, R.E. Erickson, Org. Synth., Coll. Vol. 5, 489 (1973).

R.E. Dessy, M.S. Newman, Org. Synth., Coll. Vol. 4, 484 (1963).

ジヒドロキシル化

V. VanRheenen, D.V. Cha, W.M. Hartley, Org. Synth., Coll. Vol. 6 , 342 (1988).

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B.H. McKee, D.G. Gilheany, K.B. Sharpless, Org. Synth., Coll. Vol. 9, 383 (1998).

J. Gonzalez, C. Aurigemma, L. Truesdale, Org. Synth., Coll. Vol. 10, 603 (2004).

R. Oi, K.B. Sharpless, Org. Synth., Coll. Vol. 9, 251 (1998).

水素化

R. Adams, J.W. Kern, R.L. Shriner, Org. Synth., Coll. Vol. 1, 101 (1941).

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W.F. Bruce, J.O. Ralls, Org. Synth., Coll. Vol. 2, 191 (1943).

R.M. Herbst, D. Shemin, Org. Synth., Coll. Vol. 2, 489 (1943).

D. Starr, R.M. Hixon, Org. Synth., Coll. Vol. 2, 566 (1943).

D.W. Andrus, J.R. Johnson, Org. Synth., Coll. Vol. 3, 794 (1955).

A.C. Cope, E.C. Herrick, Org. Synth., Coll. Vol. 4, 304 (1963).

D.D. Phillips, Org. Synth., Coll. Vol. 4, 313 (1963).

C.D. Gutsche, H.H. Peter, Org. Synth., Coll. Vol. 4, 887 (1963).

20

H. Takaya, T. Ohta, S. Inoue, M. Tokunaga, M. Kitamura, R. Noyori,

Org. Synth., Coll. Vol. 9, 169 (1998).

H. Lindlar, R. Dubuis, Org. Synth., Coll. Vol. 5, 880 (1973).

M.J. Taschner, T. Rosen, C.H. Heathcock, Org. Synth., Coll. Vol. 7, 226 (1990).

L.E. Overman, M.J. Brown, S.F. McCann, Org. Synth., Coll. Vol. 8, 609 (1993).