Abstract
The conversion of allyl esters into carboxylic acids using radical initiators has been achieved in high yields in aqueous media.
Key words
deallylation - esters - radical - selective - aqueous
References and Notes
1a Green TW.
Wuts PGM.
Protective Groups in Organic Synthesis
2nd ed.:
John Wiley and Sons Inc.;
New York:
1991.
1b Kocienski PJ.
Protecting Groups
Thieme;
Stuttgart:
1994.
1c Nelson TD.
Crouch RD.
Synthesis
1996,
1031
1d Nicolaou KC.
Sorensen EJ.
Classics in Total Synthesis
Wiley-VCH;
Weinheim:
1996.
2 Friedrich-Bochnitschek S.
Waldmann H.
Kunz H.
J. Org. Chem.
1989,
54:
751
3 Jungheim LN.
Tetrahedron Lett.
1989,
30:
1889
4 Zang HX.
Guibe F.
Balaviome G.
Tetrahedron Lett.
1988,
29:
623
5a Jeffrey NPD.
McCombie SW.
J. Org. Chem.
1982,
47:
587
5b Deziel R.
Tetrahedron Lett.
1987,
28:
4371
6 Kunz H.
Waldmann H.
Helv. Chim. Acta
1985,
68:
618
7 Ho T.-L.
Synth. Commun.
1978,
8:
359
8 Schmid CR.
Tetrahedron Lett.
1992,
32:
757
9 Cossy J.
Albouy A.
Scheloske M.
Pando DG.
Tetrahedron Lett.
1994,
35:
1539
10 Chavan SP.
Zubaidha PK.
Dantale SW.
Keshavaraja A.
Ramaswamy AV.
Ravindranathan T.
Tetrahedron Lett.
1996,
37:
237
11 Gajare AS.
Shingare MS.
Kulkarni VR.
Barhate NB.
Wakharkar RD.
Synth. Commun.
1998,
28:
25
12 Gajare AS.
Shaikh NS.
Bonde BK.
Deshpande VH.
J. Chem. Soc., Perkin Trans. 1
2000,
639
13a Barrett AGM.
Lebold SA.
Zang XA.
Tetrahedron Lett.
1989,
30:
7317
13b Garay RO.
Cabaleiro MC.
14a Davis ME.
Acc. Chem. Res.
1993,
26:
11
14b Holderich W.
Hesse M.
Naumann F.
Angew. Chem., Int. Ed. Engl.
1988,
27:
226
14c Suib SL.
Chem. Rev.
1993,
93:
803
14d Sachtler WMH.
Acc. Chem. Res.
1993,
26:
383
14e Kumar P.
Kumar R.
Pandey B.
J. Indian Inst. Sci.
1994,
74:
293
15 Perchyonok VT.
Tetrahedron Lett.
2006,
47:
5163 ; and references cited therein
16 Escoubet S.
Gastaldi S.
Bertrand M.
Eur. J. Org. Chem.
2005,
3855 ; and references cited therein
17 Authors are grateful to the referees for the suggestion of a plausible mechanism and valuable insight into the kinetics of the acyl radicals.
18a Esposti S.
Dondi D.
Fagnoni M.
Albini A.
Angew. Chem. Int. Ed.
2007,
46:
2531
18b Nambu H.
Hata K.
Matsugi M.
Kita Y.
Chem. Commun.
2002,
1082
19a Pfenninger J.
Heuberger C.
Graf W.
Helv. Chim. Acta
1980,
63:
2328
19b Boger DL.
Mathvink RJ.
J. Org. Chem.
1988,
53:
3377
19c Crich D.
Fortt SM.
Tetrahedron
1989,
45:
6581
19d Schwartz CE.
Curran DP.
J. Am. Chem. Soc.
1990,
112:
9272
19e Boger DL.
Mathvink RJ.
J Org. Chem.
1992,
57:
1429
19f Betty D.
Crich D.
J. Chem. Soc., Perkin Trans. 1
1992,
3193
19g Crich D.
Chen C.
Hwang J.-H.
Yuan H.
Papadatos A.
Walter RI.
J. Am. Chem. Soc.
1994,
116:
8937
19h Hayes CJ.
Pattenden G.
Tetrahedron Lett.
1996,
37:
271
19i Chen L.
Gill GB.
Pattenden G.
Simonian H.
20a Chatgilialoglu C.
Lucarini M.
Tetrahedron Lett.
1995,
36:
1299
20b Chatgilialoglu C.
Ferreri C.
Lucarini M.
Pedrielli P.
Pedulli GF.
Organometallics
1995,
14:
2672
21 Denisova TG.
Denisov ET.
Kinet. Catal.
2004,
45:
301 ; and references cited therein
22 Competition experiments with a 1:1 mixture of the methyl ester and allyl ester of 2-(4-isobutylphenyl)propanoic acid (Table
[2 2 O, respectively.
