First Synthesis of a Conformationally Restricted 2,2’-Bipyrrole

Abstract

A seven-step procedure was developed for the preparation of the cyclooctadiene-annulated 2,2’-bipyrrole 14, starting from commercially available benzyl bromoacetate 6 and adiponitrile 7. Although all transformations carried out had to be sufficiently selective to produce the desired functionalities on both sites of the respective dipyrroles, acceptable to good yields were observed throughout the synthesis. The paper reports synthetic and spectroscopic details of the new compounds.

Key words

2,2’-bipyrroles - pyrroles - conformation - heterocycles - ring closure

References

• 1 For a recent overview, see: Fürstner A. Fürstner A. Grabowski J. Lehmann CW. Kataoka T. Nagai K. ChemBioChem.  2001,  2:  60 and Ref. 4,9a,¹0cited therein 
• 2a For an overview, see: Sessler JL. Weghorn SJ. Expanded, Contracted & Isomeric Porphyrins   Elsevier; Oxford: 1997. 
• 2b Setsune J.-i. Maeda S. J. Am. Chem. Soc.  2000,  122:  12405 
• 2c Wytko JA. Michels M. Zander L. Lex J. Schmickler H. Vogel E. J. Org. Chem.  2000,  65:  8709 
• 3a Drews A. Schönemeier T. Seggeweis S. Breitmaier E. Synthesis  1998,  749 
• 3b Vogel E. Bröring M. Weghorn SJ. Scholz P. Deponte R. Lex J. Schmickler H. Schaffner K. Braslavsky SE. Müller M. Pörting S. Fowler CJ. Sessler JL. Angew. Chem., Int. Ed. Engl.  1997,  36:  1651 ; Angew. Chem. 1997, 109, 1725
• 3c Morosini P. Scherer M. Meyer S. Lynch V. Sessler JL. J. Org. Chem.  1997,  62:  8848 
• 3d Vogel E. Binsack B. Hellwig Y. Erben C. Heger A. Angew. Chem., Int. Ed. Engl.  1997,  36:  2612;  Angew. Chem. 1997, 109, 2725
• 3e Sessler JL. Weghorn SJ. Lynch V. Fransson K. J. Chem. Soc., Chem. Commun.  1994,  1289 
• 3f Sepulveda-Boza S. Breitmaier E. Liebigs Ann. Chem.  1983,  894 
• 3g Kazlauskas K. Marwood FF. Murphy PT. Wells RJ. Aust. J. Chem.  1982,  35:  215 
• 3h Dolphin D. Grigg R. Johnson AW. Leng J. J. Chem. Soc.  1965,  1460 
• 3i Grigg R. Johnson AW. J. Chem. Soc.  1964,  3315 
• 3j Bullock E. Grigg R. Johnson AW. Wasley JWF. J. Chem. Soc.  1963,  2326 
• 3k Johnson AW. Kay IT. Rodrigo R. J. Chem. Soc.  1963,  2336 
• 4 Sessler JL. Hoehner MC. Synlett  1994,  211 
• 5a Scrosati B. Applications of Electroactive Polymers   Chapman & Hall; London: 1993. 
• 5b Rodriguez J. Grande HJ. Otero TF. In Handbook of Organic Conductive Molecules and Polymers   Nalwa HS. Wiley; New York: 1997.  p.415 
• 6 Che C.-M. Wan C.-W. Lin W.-Z. Zhou Z.-Y. Lai W.-Y. Lee S.-T. Chem. Commun.  2001,  721 
• 7a Johnson AW. Price R. J. Chem. Soc.  1960,  1649 
• 7b Bröring M. Synthesis  2000,  1291 
• 7c Bröring M. Griebel D. Hell C. Pfister A. J. Porphyrins Phthalocyanines  2001,  5:  708 
• 8a Dolphin D. Harris RLN. Huppatz JL. Johnson AW. Kay IT. Leng J. J. Chem. Soc. (C)  1966,  98 
• 8b Bröring M. Brandt CD. Lex J. Humpf H.-U. Bley-Escrich J. Gisselbrecht J.-P. Eur. J. Inorg. Chem.  2001,  2549 
• 9 Zhang Y. Thompson A. Rettig SJ. Dolphin D. J. Am. Chem. Soc.  1998,  120:  13537 
• 10a Vogel E. Pure Appl. Chem.  1993,  65:  143 
• 10b Berlin A. Bradamante S. Ferraccioli R. Pagani GA. Sannicolò F. J. Chem. Soc., Chem. Commun.  1987,  1176 
• 11 Paine JB. Dolphin D. Can. J. Chem  1978,  56:  1710 
• 12 Tang J. Verkade JG. J. Org. Chem.  1994,  59:  7793