Nitrile to acid

hydrolysis of nitrile is very sensitive to the hinderance around the nitrile.

1. KOH in MeOH/water.
140C
2. KOH in ethylene glycol. or diethylene glycol.
200C or 250C.
3. KOH/H2O2/water/EtOH
100C, more reactive toward hindered nitrile.

4. HCl or H2SO4 in water or MeOH
strong acid needed. not compatible with ether, alkene.

5. DIBAlH then oxidation.
6. o-phthalic anhydride.
7. Microwave/ phthalic acid.
8. reductive removal of the nitrile by LidBB or LN, then trap the anion by CO2.

allylic oxidation

1. MnO2/DCM.rt
can selectively oxidize allylic alcohols with primary alcohols untouched.

2. SeO2
selectively oxidize allylic H to alcohol.
1. 95% EtOH, reflux
2. DCM, t-BuOOH
3. 1,4-dioxane, t-BuOOH.
4. xylene(toluene), reflux
Acid is known to accelerate the rxn rate.

How do you prepare nmr shifts for publication?

Found a new software which can format the peaks/integration/J coupling for you.
acd/1d nmr assistant.

you only need to assign the desired peaks, sometimes the integration, j constant will be calculated automatically.
example output:
¹H NMR (CHLOROFORM-d) d ppm 0.58 (3 H, d, J=7.0 Hz), 0.88 (9 H, m), 0.95 (11 H, m), 1.05 (6 H, m), 1.28 (6 H, m), 1.46 (2 H, m), 1.83 (9 H, m), 2.19 (6 H, m), 2.44 (2 H, m), 3.04 (1 H, d, J=9.0 Hz), 3.13 (1 H, m), 3.80 (1 H, d, J=5.1 Hz), 7.28 (15 H, m), 7.42 (9 H, m)

READY for publication!!!!!!!!!!!!!!!!!!

For carbon nmr, you can also get a peak list:
example output:
(ppm)
20.0
25.1
28.2
31.2
32.4
33.7
52.7
58.2
61.1
67.0
87.4
117.6
143.4
174.9


added (7-2009)
both mestrec and mestrenova have the function of generating decent NMR formatted report for acs or wiley.