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Synthesis and Structure of Diboraporphyrinogenes
Author(s) -
Eckert Anke,
Pritzkow Hans,
Siebert Walter
Publication year - 2002
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/1099-0682(200208)2002:8<2064::aid-ejic2064>3.0.co;2-4
Subject(s) - chemistry , substituent , boron , thiophene , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , financial economics , economics
Reactions of 5,5′‐dilithiated 1,1‐bis(2‐thienyl)ethane ( 3 ) with different substituted dichloroboranes led to the novel 5,15‐diboraporphyrinogenes 5 − 8 , in good yields. Amino groups at the boron atoms stabilize the macrocycles 5 − 7 , whereas the first organyl‐stabilized diboraporphyrinogene 8 contains the 2,3,5,6‐tetramethylphenyl substituent at the boron atoms. A [3+1] approach yields the 5,10‐diboraporphyrinogene 13 by treating 2,5‐bis[1‐(5‐lithio‐2‐thienyl)ethyl]thiophene ( 4 ) with the 2,5‐diborylthiophene derivative 9 . Analogously, the mixed 5,10‐diboraporphyrinogenes 15 and 16 are formed from 4 and 2,5‐diborylfuran 11 and 2,5‐diboryl‐ N ‐methylpyrrole 12 , respectively. The constituents of the new compounds follow from spectroscopic and structural data. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)