化学官能团相互转换大全(part2)

JA C S, 1972, 94, 7159.

L A H ------------ alm ost all: ald, ketone, acie, ester, acyl X, anhydride

N aB H4 --------------- not for acid, ester (but L iB H4 w ork for ester)

B2H6 --------------- not for ester, acyl X, anhydride;

from top:

L iA lH4; N aB H4; N a / N H3

A l (O i Pr)3 / i PrO H ----------- M eerw ein-Pondorf-V erley rxn

IrC l4 / i P rO H / P(O M e)3 ------ H enbest rxn

L iB H(sec Bu)3 ------------------ H. C. B row n

from bottom:

(2). stereoselective:

(1). regioselective:

3-h

(3). H C H O reagent:

M e C H O M e

O H

H C H O

JA C S, 1935, 511, 903.

C H3C H O C(C H2O H)4

2

O rg.Syn, 1925, 4, 53.

H C H O / K O H

H C H O / C a(O H)2

S ynthesis, 1994, 1007.

Ph

N O2

O

Ph

N O2

H O H

B H / SM e

JO C, 2001, 66, 7514.

JO C, 2003, 68, 2030.

O

B H3 / T H F

99.5 % trans

solvent: T H F, S M e2

3-i

R3B, H O C H2C H2O H // H2O2 // N aO H

JO C, 1986, 51, 4925.

C O R

R

R3B

R

R

R

R

R3C B O

H O C H2C H2O H

R3C B

O

O

H2O2

O H

R3

H

O B

O

O

R3C

H2O

R3C O H

p ra c tic e

3-k O

O H

H

O H

O H

O

O H

O H

H

O H

O H

JO C , 1967, 32

, 3452.

H 2O 2: dangerous,

skin w hiten, m etal decom pose

H g (O A c)2: toxic, hard to rem ove (3). B 2H 6, H 2O 2 / O H -, H 2O

(2). H g(O A c)2, H 2O // N aB H 4(1). H 3O +

3-j

3-j.13-j.2hydration:

(1). K M nO 4 / N aO H (2). O sO 4

(3). H 2O 2/H C O 2H (4). N a / E tO H

H H

cis tran cis +tran

cis

M e 2N

N

N

C H 3H

C l

H 3

N C H 3

H H N C H 3

C

H H

+

N

C H 3

C l N H H C H O

C

O O H

A C H 21. L A H R 3C N H 2R

C

N R 2

R C N H R R 3C

O H

R 2C O H R C O H R C N H 2tertiary

secondary prim ary C om pare nom enclature class:

not a very useful reaction

C -N

C -H C -N C -X C -O H C =O

C =C 4-a

b

c d e

f g 4-a

SO 2N H 2Ph I

O A c O A c

S O O

N H S O

O

N I P h Fe (T PP )C l

S O O

N H 2(insertion)

T P P

N N

N

N

P h

2. N aN 3N C O

1. SO 2C l 2O 2

C

C

O O h i

C N C (O )X C -C (O )X