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A variety of Group 15 element porphyrins bearing element-carbon bond(s) were synthesized mainly by use of R 3 Al as an alkylating reagent. The synthetic methods, X-ray crystallographic structures, some spectral data ( 1 H-NMR), and some reactions of the porphyrins were surveyed. One of the most important properties of these compounds is the formation of the element-oxygen double bond in the phosphorus and arsenic porphyrins. The bond formation was confirmed by X-ray crystallographic analysis of (OEP)P(Et)( O). The P O bond length of [(OEP)P(Et)(OH)] + Cl -and (OEP)P(Et)( O) was 1.636(4) and 1.484(9) A , , respectively (cf. P O bond length of Ph 3 P O is 1.483 A , ). Since (OEP)P(Et)( O) was stabilized by the formation of the P O bond, the OH proton of [(OEP)PEt(OH)] + Cl -was acidic (pK a ca. 7 -8). Although the similar formation of the double bond was not observed in the corresponding antimony compounds, the corresponding As O formation was observed in newly synthesized (OEP)As(R)( O). The relatively high acidity of the OH protons in [(OEP)M(R)(OH)] + X -(M= P, As) {and the stability of the (OEP)M(R)( O)} would be the main reason for the relatively high reactivity of phosphorus an

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Author

Yohsuke Yamamoto; Kin-ya Akiba

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

2000

Language

EN

Field

Chemistry (Physical Sciences)