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Synthesis 2008(15): 2412-2416
DOI: 10.1055/s-2008-1067187
DOI: 10.1055/s-2008-1067187
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Phosphaisocoumarin Acids via Me3SiX-Mediated Dealkylation Reaction
Further Information
Received
25 March 2008
Publication Date:
25 July 2008 (online)
Publication History
Publication Date:
25 July 2008 (online)
Abstract
The dealkylation of phosphaisocoumarin esters was studied under various conditions. An effective way to synthesize phosphaisocoumarin acids was developed via the reaction of phosphaisocoumarin esters with Me3SiBr in chloroform followed by treatment with methanol, or with Me3SiCl and NaI in acetonitrile followed by hydrolysis, under mild conditions in good to excellent yields.
Key words
synthesis - hydrolysis - dealkylation - phosphorus heterocycle
-
1a
Handbook of Organophosphorus Chemistry
Engel R. Marcel Dekker; New York: 1992. Chap. 11. -
1b
A Guide
to Organophosphorus Chemistry
Quin LD. Wiley; New York: 2000. Chap. 11. -
2a
Peng A.-Y.Ding Y.-X. J. Am. Chem. Soc. 2003, 125: 15006 -
2b
Peng A.-Y.Ding Y.-X. Org. Lett. 2004, 6: 1119 -
2c
Peng A.-Y.Ding Y.-X. Tetrahedron 2005, 61: 10303 - 3
Eberhard A.Westheimer FH. J. Am. Chem. Soc. 1965, 87: 253 - 4
Mereyala HB.Pathuri G. Synthesis 2006, 2944 -
5a
Macomber RS.Krudy GA. J. Org. Chem. 1981, 46: 4038 -
5b
Miles JA.Grabiak RC.Cummins C. J. Org. Chem. 1982, 47: 1677 -
5c
Mukhametov FS.Korshin EE.Korshunov RL.Efremov YuY.Zyablikova TA. Zh. Obshch. Khim. 1986, 56: 1781 ; Chem. Abstr. 1987, 107, 576105 -
5d
Nifant’ev EE.Popkova TN.Kukhareva TS.Bekker AR. Zh. Obshch. Khim. 1988, 58: 1550 ; Chem. Abstr. 1989, 110, 212940 -
6a
Fernandez MC.Diaz A.Guillin JJ.Blanco O.Ruiz M.Ojea V. J. Org. Chem. 2006, 71: 6958 -
6b
Ruiz M.Fernandez C.Diaz A.Quintela JM.Ojea V. J. Org. Chem. 2003, 68: 7634 -
6c
Stoianova DS.Hanson PR. Org. Lett. 2001, 3: 3285 - 7
Ghosh S.Tuhina K.Bhowmik DR.Venkateswaran RV. Tetrahedron 2006, 63: 644 - 8
Peng A.-Y.Ding Y.-X. Heteroat. Chem. 2005, 16: 529 - 9
Kenner W. J. Chem. Soc. 1955, 522