Abstract
A combination of 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) and acetic acid has been utilized for photoinduced reductive transformation of α,β-epoxy ketones to β-hydroxy ketones. Study on photoreactions using several proton donors revealed that acetic acid is superior to other proton donors such as HCl, p- TsOH, MeOH, and water. 1,3-Dimethyl-2-phenylbenzimidazolium was produced in the reaction with acetic acid while N -benzoyl-N ,N ′-dimethyl-o -phenylenediamine was formed in aqueous solvents. When THF solutions containing aryl carbonyl possessing α,β-epoxy ketones and DMPBI and acetic acid were irradiated (λ > 280 nm), β-hydroxy ketones were isolated in good to excellent yields. Photosensitized conditions (λ > 340 nm) were employed for the reactions of alkyl carbonyl possessing α,β-epoxy ketones.
Key words
photoinduced electron transfer - 1,3-dimethyl-2-phenylbenzimidazoline - acetic acid - α,β-epoxy ketones - reductive ring opening - β-hydroxy ketones
References
1a Padwa A.
Organic Photochemistry
Vol 1:
Chapman OL.
Marcel Dekker;
New York:
1967.
p.91
1b Griffin GW.
Organic Photochemistry
Vol 3:
Chapman OL.
Marcel Dekker;
New York:
1973.
p.115
1c Nastashi M.
Streith J.
Rearrangements in Ground and Excited States
Vol. 3:
deMayo P.
Academic Press;
New York:
1980.
p.445
2a Bodforss S.
Chem. Ber.
1918,
51:
214
2b Johnson CK.
Domony B.
Reush W.
J. Am. Chem. Soc.
1963,
85:
3984
2c Dunston JM.
Yates P.
Tetrahedron Lett.
1964,
505
2d Padwa A.
Tetrahedron Lett.
1964,
813
2e Simikin RD.
Zimmerman HE.
Tetrahedron Lett.
1964,
1847
2f Zimmerman HE.
Cowley BR.
Tseng CY.
Wilson JW.
J. Am. Chem. Soc.
1964,
86:
947
2g Markos CS.
Reush W.
J. Am. Chem. Soc.
1967,
89:
3363
2h Pappas SP.
Gresham RM.
Miller MJ.
J. Am. Chem. Soc.
1970,
92:
5797
2i Padwa A.
Eisenhardt W.
J. Am. Chem. Soc.
1971,
93:
1400
2j Pete JP.
Viriot-Villaum ML.
Bull. Soc. Chim. Fr.
1971,
3699
2k Pappas SP.
Bao LO.
J. Am. Chem. Soc.
1973,
95:
7906
2l Venkataramani PS.
Saxena NK.
Srinivasan R.
Ors J.
J. Org. Chem.
1976,
41:
2784
2m Dewar DJ.
Sutherland RG.
J. Chem. Soc., Perkin Trans. 2
1977,
1522
2n Muzart J.
Pete JP.
Tetrahedron Lett.
1977,
303:
307
2o Lee GA.
J. Org. Chem.
1978,
43:
4256
2p Hallet P.
Muzart J.
Pete JP.
J. Org. Chem.
1981,
46:
4275
2q Paquette LA.
Nitz TJ.
Ross RJ.
Springer JP.
J. Am. Chem. Soc.
1984,
106:
1446
2r Kumar CV.
Das PK.
O’Sullivan WI.
Ege SN.
Griffin GW.
J. Chem. Soc., Perkin Trans. 2
1984,
1745
2s Kumar CV.
Ramaiah D.
Das PK.
George MV.
J. Org. Chem.
1985,
50:
2818
3a Fieser LF.
J. Am. Chem. Soc.
1953,
75:
4395
3b Robinson CH.
Henderson R.
J. Org. Chem.
1972,
37:
565
3c Weile GR.
McMorris TC.
J. Org. Chem.
1978,
43:
3942
3d Shapiro EL.
Gentles M.
Kabasakalian P.
Magatti A.
J. Org. Chem.
1981,
46:
5017
3e Osuka A.
Takaoka K.
Suzuki H.
Chem. Lett.
1984,
271
3f McChesney JD.
Thompson TN.
J. Org. Chem.
1985,
50:
3473
3g Molander GA.
Hahn G.
J. Org. Chem.
1986,
51:
2596
3h Miyashita M.
Suzuki T.
Yoshikoshi A.
Tetrahedron Lett.
1987,
28:
4293
3i Inokuchi T.
Kusumoto M.
Torii S.
J. Org. Chem.
1990,
55:
1548
3k Hasegawa E.
Ishiyama K.
Kato T.
Horaguchi T.
Shimizu T.
J. Org. Chem.
1992,
57:
5352
3l Engman L.
Stern D.
J. Org. Chem.
1994,
59:
5179
3m 2 TiCl): Hardouin C.
Chevallier F.
Rousseau B.
Doris E.
J. Org. Chem.
2001,
66:
1046
4a Hasegawa E.
Ishiyama K.
Horaguchi T.
Shimizu T.
J. Org. Chem.
1991,
56:
1631
4b Hasegawa E.
Ishiyama K.
Horaguchi T.
Shimizu T.
Tetrahedron Lett.
1991,
32:
2029
5 Cossy J.
Bouzide A.
Ibhi S.
Aclinou P.
Tetrahedron
1991,
47:
7775
6 Hasegawa E.
Ishiyama K.
Fujita T.
Kato T.
Abe T.
J. Org. Chem.
1997,
62:
2396
7a Chikashita H.
Itoh K.
Bull. Chem. Soc. Jpn.
1986,
59:
1747
7b Chikashita H.
Ide H.
Itoh H.
J. Org. Chem.
1986,
51:
5400
7c Chen J.
Tanner DD.
J. Org. Chem.
1988,
53:
3898
7d Chen J.
Tanner DD.
J. Org. Chem.
1989,
54:
3842
7e Tanner DD.
Chen J.
Chen L.
Luelo C.
J. Am. Chem. Soc.
1991,
113:
8074
7f Tanner DD.
Chen J.
J. Org. Chem.
1992,
57:
662
7g Tanner DD.
Chen J.
Luelo C.
Peters PM.
J. Am. Chem. Soc.
1992,
114:
713
8a Hasegawa E.
Kato T.
Kitazume T.
Yanagi K.
Hasegawa K.
Horaguchi T.
Tetrahedron Lett.
1996,
37:
7079
8b Hasegawa E.
Yoneoka A.
Suzuki K.
Kato T.
Kitazume T.
Yanagi K.
Tetrahedron
1999,
55:
12957
9 Okada K.
Okamoto K.
Oda M.
J. Am. Chem. Soc.
1988,
110:
8736
10 Mann CK.
Barnes KK.
Electrochemical Reactions in Nonaqueous Systems
Marcel Dekker;
New York:
1973.
p.283
11 Spectral and elemental analysis data of 1b , 1d , 1k , 1l and 2b , 2d , 2k , 2l were reported as Supplementary Material of reference 3k.
12 Zweig A.
Maure AH.
Roberts BG.
J. Org. Chem.
1967,
32:
1322
13a Craig JC.
Ekwuribe N.
Fu CC.
Walker KAM.
Synthesis
1981,
303
13b Lee I.-SH.
Jeoung EH.
Kreevoy MM.
J. Am. Chem. Soc.
1997,
119:
2722
