134
Vol. 59, No. 1
(100 mg, 0.56 mmol) was treated with TBAB (1.8 mg, 0.0056 mmol) and
Oxone® (209 mg, 0.64 mmol) in CH3CN–H2O (2 : 1, 1.4 ml) to give 2-
azidomethyl-1,4-benzoquinone (2i) (86 mg, 95%) as yellow needles.
TBAB Catalyzed Oxidation of 1j Following the general procedure, 1j
(28 mg, 0.1 mmol) was treated with TBAB (0.3 mg, 0.001 mmol) and
Oxone® (37 mg, 0.06 mmol) in CH3CN–H2O (2 : 1, 0.25 ml) to give 2-(3,6-
dioxocyclohexa-1,4-dienylmethyl)isoindole-1,3-dione (2j) (25 mg, 95%) as
yellow needles.
TBAB Catalyzed Oxidation of 1k Following the general procedure, 1k
(105 mg, 0.68 mmol) was treated with TBAB (4.4 mg, 0.012 mmol) and
Oxone® (252 mg, 0.41 mmol) in CH3CN–H2O (2 : 1, 2 ml) to give 2-hydroxy
-
methyl-1,4-benzoquinone (2k) (90 mg, 96%) as yellow crystals, mp 76—
77 °C (CH2Cl2–hexane) (lit.17) 76—77 °C). IR (KCl) cmꢁ1: 1655, 1640,
1590. 1H-NMR (300 MHz, CDCl3) d: 2.57 (1H, br s), 4.56 (2H, d, Jꢂ2 Hz),
6.7—6.9 (3H, m).
TBAB Catalyzed Oxidation of 1l Following the general procedure, 1l
(174 mg, 1 mmol) was treated with TBAB (16 mg, 0.05 mmol) and Oxone®
(369 mg, 0.6 mmol) in CH3CN–H2O (2 : 1, 2.5 ml) to give 1,4-naphtho-
quinone (2l) (168 mg, quant.) as yellow crystals, which was directly identical
to the commercial sample supplied by Tokyo Chemical Industry (TCI) Co.,
Ltd.
Chart 3
Experimental
Melting points are uncorrected. IR spectra were recorded using JASCO
1
FT/IR-460 Plus spectrophotometer. H-NMR spectra were determined with
Varian Gemini 300 (300 MHz) spectrometers, tetramethylsilane as an inter-
nal standard. TBAB and Oxone® were purchased from Aldrich and Wako
Pure Chemical Industries, Ltd., respectively. Both were used as received.
Phenols (1a—f, k) and 4-methoxy-1-naphthol (1l) were commercially avail-
able. Other phenols (1g—j) were prepared by the usual methods.8) The re-
sulting p-quinones (2a—j) were directly identical to authentic samples pre-
pared by our previous reported hypervalent iodine oxidation of the corre-
sponding p-alkoxyphenols.8)
TBAB Catalyzed Oxidation of 1a, General Procedure A suspension
of 1a (124 mg, 1 mmol), TBAB (1.5 mg, 0.005 mmol) and Oxone® (368 mg,
0.6 mmol) in CH3CN–H2O (2 : 1, 2.5 ml) was stirred at room temperature for
50 min. The mixture was diluted with ethyl acetate and washed with water,
dried, and concentrated to give pure 1,4-benzoquinone (2a) (98 mg, 91%) as
yellow crystals.
References and Notes
1) “The Chemistry of the Quinonoid Compounds,” Vol. 2, Parts 1 and 2,
ed. by Patai S., Rappoport Z., John Wiley & Sons, Chichester, 1988.
2) “Naturally Occurring Quinones IV Recent Advances,” ed. by Thom-
son R. H., Blackie Academic & Professional, London, 1997.
3) Dudfield P. J., “Comprehensive Organic Synthesis,” Vol. 7, ed. by
Trost B. M., Fleming I., Elsevier, Oxford, 1991, pp. 345—356.
4) Review: Gallagher P. T., Contemp. Org. Synth., 3, 433—446 (1996).
5) Review: Akai S., Kita Y., Org. Prep. Proced. Int., 30, 603—629
(1998).
6) Review: Owton W. M., J. Chem. Soc., Perkin Trans. 1, 1999, 2409—
2420 (1999).
7) Yakura T., Konishi T., Synlett, 2007, 765—768 (2007).
8) Yakura T., Tian Y., Yamauchi Y., Omoto M., Konishi T., Chem. Pharm.
Bull., 57, 252—256 (2009).
9) Review: Marcotullio M. C., Epifano F., Curini M., Trends Org. Chem.,
10, 21—34 (2003).
10) Schulze A., Giannis A., Synthesis, 2006, 257—260 (2006).
11) Koo B.-S., Lee C. K., Lee K.-J., Synth. Commun., 32, 2115—2123
(2002).
TBAB Catalyzed Oxidation of 1b Following the general procedure, 1b
(138 mg, 1 mmol) was treated with TBAB (1.5 mg, 0.005 mmol) and Oxone®
(368 mg, 0.6 mmol) in CH3CN–H2O (2 : 1, 2.5 ml) to give 2a (99 mg, 92%)
as yellow crystals.
TBAB Catalyzed Oxidation of 1c Following the general procedure, 1c
(166 mg, 1 mmol) was treated with TBAB (1.5 mg, 0.005 mmol) and Oxone®
(368 mg, 0.6 mmol) in CH3CN–H2O (2 : 1, 2.5 ml) to give 2a (99 mg, 92%)
as yellow crystals.
12) Schulze A., Pagona G., Giannis A., Synth. Commun., 36, 1147—1156
(2006).
13) Yan P., Wang R., Wu S., Lei Z., Catal. Commun., 9, 406—408 (2008).
14) Wu S., Ma H., Yan P., Wang J., Ding J., Lei Z., Lett. Org. Chem., 6,
424—427 (2009).
15) Podgorsˇek A., Zupan M., Iskra J., Angew. Chem., Int. Ed., 48, 8424—
8450 (2009).
16) When we tried a reaction of p-nitrobenzyl alcohol with 10 mol% of
TBAB and 1 eq of Oxone® in CH3CN–H2O, the corresponding alde-
hyde (37%) and acid (38%) were obtained after 45 min at 70 °C.
TBAB Catalyzed Oxidation of 1d Following the general procedure, 1d
(110 mg, 1 mmol) was treated with TBAB (1.5 mg, 0.005 mmol) and Oxone®
(368 mg, 0.6 mmol) in CH3CN–H2O (2 : 1, 2.5 ml) to give 2a (98 mg, 91%)
as yellow crystals.
TBAB Catalyzed Oxidation of 1e Following the general procedure, 1e
(180 mg, 1 mmol) was treated with TBAB (6.5 mg, 0.02 mmol) and Oxone®
(368 mg, 0.6 mmol) in CH3CN–H2O (2 : 1, 2.5 ml) to give 2-tert-butyl-1,4-
benzoquinone (2e) (162 mg, 99%) as orange crystals.
TBAB Catalyzed Oxidation of 1f Following the general procedure, 1f
(90 mg, 0.31 mmol) was treated with TBAB (2 mg, 0.0062 mmol) and
Oxone® (114 mg, 0.19 mmol) in CH3CN–H2O (2 : 1, 0.75 ml) to give 2,5-bis-
(1,1-dimethylbutyl)-1,4-benzoquinone (2f) (86 mg, quant.) as orange crys-
tals.
TBAB Catalyzed Oxidation of 1g Following the general procedure, 1g
(120 mg, 0.5 mmol) was treated with TBAB (1.6 mg, 0.005 mmol) and
Oxone® (185 mg, 0.3 mmol) in CH3CN–H2O (2 : 1, 1.25 ml) to give 3,6-
dioxocyclohexa-1,4-dienylmethyl 2,2-dimethylpropanoate (2g) (110 mg,
98%) as yellow crystals.
TBAB Catalyzed Oxidation of 1h Following the general procedure, 1h
(80 mg, 0.2 mmol) was treated with TBAB (1.9 mg, 0.006 mmol) and
Oxone® (73 mg, 0.12 mmol) in CH3CN–H2O (2 : 1, 0.5 ml) to give 2-(tert-
butyldiphenylsilyloxymethyl)-1,4-benzoquinone (2h) (73 mg, 95%) as yel-
low solid.
17) Tamura Y., Yakura T., Tohma H., Kikuchi K., Kita Y., Synthesis, 1989,
126—127 (1989).
18) Zalomaeva O. V., Kholdeeva O. A., Sorokin A. B., Green Chem., 8,
883—886 (2006).
19) Yakura T., Omoto M., Chem. Pharm. Bull., 57, 643—645 (2009).
20) Yakura T., Yamauchi Y., Tian Y., Omoto M., Chem. Pharm. Bull., 56,
1632—1634 (2008).
21) Yakura T., Omoto M., Yamauchi Y., Tian Y., Ozono A., Tetrahedron,
66, 5833—5840 (2010).
TBAB Catalyzed Oxidation of 1i Following the general procedure, 1i