Polymer-bound Phenothiazine 양이온 라디칼의 합성

진명종; 김상한

Journal of the Korean Industrial and Engineering Chemistry, Vol.6, No.2, 283-287, April, 1995

Export Citation

Polymer-bound Phenothiazine 양이온 라디칼의 합성

Synthesis of Polymer-bound Phenothiazine Cation Radical

진명종, 김상한

초록

Phenothiazine aminium hexachloroantimonate 양이온 라디칼이 불용성 폴리머체에 정량적으로 접합되어졌다. 그 폴리머 양이온 라디칼은 쉽게 [C₅H₅Fe(CO)₂]₂내의 금속결합을 끊을 수 있다는 것과 Bu₄NPF₆와 음이온 교환하여 합성에 더 유용한 phenothiazine aminium hexafluorophosphate로 전환될 수 있음을 알 수 있었다.

Phenothiazine aminium hexachloroantimonate was quantitatively incorporated into insoluble cross-linked polystyrene framework. The polymer cation radical was found to readily cleave metal-metal bond in [C₅H₅Fe(CO)₂)]₂ as an effective one-electron oxidant and undergo anion exchange with Bu₄NPF₆ to convert a more synthetically useful phenothiazine aminium hexafluorophosphate.

[References]

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[1] Robert WI, J. Am. Chem. Soc., 77, 5999 (1955)

[2] Bell FA, Ledwith A, Sherrington DC, J. Chem. Soc.-Chem. Commun., 2719 (1969)

[3] Bauld NL, Bellville DJ, Wirth DD, J. Am. Chem. Soc., 103, 718 (1981)

[4] Gassman PG, Singleton DA, J. Am. Chem. Soc., 106, 7993 (1984)

[5] Bauld NL, Harirchian B, Reynolds DW, White JC, J. Am. Chem. Soc., 110, 8111 (1988)

[6] Cummins CC, Kegley SE, ACS National Meeting, Denver. Co., Inorg. Abstr., 137 (1987)

[7] Hodge P, Sherrington DC, "Polymer-Supported Reactions in Organic Synthesis," Wiley, New York (1980)

[8] Akelah A, Sherrington DC, Chem. Rev., 81, 557 (1981)

[9] Akleah A, Synthesis, 43 (1981)

[10] Heitz W, Adv. Polym. Sci., 23, 1 (1977)

[11] Campaigne E, Archer WL, Org. Synth., 4, 217 (1963)

[12] Greenwald R, Chaykovsky M, Corey EJ, J. Org. Chem., 28, 1128 (1963)

[13] Parrinello G, Stille JK, J. Am. Chem. Soc., 109, 7122 (1987)

[14] Parrinello G, Deschenaux R, Sille JK, J. Org. Chem., 51, 4189 (1986)

[15] Cotton TS, Wilkinson G, J. Inorg. Nucl. Chem., 1, 165 (1955)

[16] Lennon P, Rosan AM, Rosenblum M, J. Am. Chem. Soc., 99, 8426 (1977)

[17] Chang TCT, Rosenblum M, Samuels SB, J. Am. Chem. Soc., 102, 5930 (1980)

[18] Chang TCT, Foxman BM, Rosenblum M, Stockman C, J. Am. Chem. Soc., 103, 7361 (1981)

[19] Reger DL, McElligott PJ, J. Am. Chem. Soc., 102, 5923 (1980)

[20] Reger DL, Coleman CJ, Inorg. Chem., 18, 3155 (1979)

[21] Reger DL, Coleman CJ, McElligott PJ, J. Org. Chem., 171, 73 (1979)