Porpholactams and chlorolactams: replacement of a β,β′-double bond in meso-tetraphenyl-porphyrin and -chlorin by a lactam moiety

被引:22
作者
Akhigbe, Joshua [1 ]
Haskoor, John [1 ]
Zeller, Matthias [2 ]
Brueckner, Christian [1 ]
机构
[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA
[2] Youngstown State Univ, Dept Chem, Youngstown, OH 44555 USA
基金
美国国家科学基金会;
关键词
COMPLEXES; CONFUSION; CHEMISTRY; COMPOUND; POSITION; BASE;
D O I
10.1039/c1cc12955d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction of meso-tetraphenylporpholactone with hydrazine converts the lactone moiety to an N-aminolactam. It also reduces the opposite pyrrolic moiety of both the starting material and the N-aminolactam, generating chlorin-like chlorolactone and N-aminochlorolactam, respectively. Reductive N-N cleavage of the N-aminoporpholactam generates the parent porpholactam.
引用
收藏
页码:8599 / 8601
页数:3
相关论文
共 25 条
[1]   Unexpected hydroxylamine-induced ring-closure reactions of meso-tetraphenylsecochlorin bisaldehyde [J].
Akhigbe, Joshua ;
Peters, Gretchen ;
Zeller, Matthias ;
Brueckner, Christian .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2306-2313
[2]  
[Anonymous], 2000, PORPHYRIN HDB
[3]   Fragmentation and cleavage reactions mediated by SmI2.: Part 1:: X-Y, X-X and C-C substrates [J].
Bradley, D ;
Williams, G ;
Blann, K ;
Caddy, J .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2001, 33 (06) :565-+
[4]   A spectroscopic and computational study of the singlet and triplet excited states of synthetic β-functionalized chlorins [J].
Brückner, C ;
McCarthy, JR ;
Daniell, HW ;
Pendon, ZD ;
Ilagan, RP ;
Francis, TM ;
Ren, L ;
Birge, RR ;
Frank, HA .
CHEMICAL PHYSICS, 2003, 294 (03) :285-303
[5]   NOVEL HETEROCYCLIC-SYSTEMS FROM SELECTIVE OXIDATION AT THE BETA-PYRROLIC POSITION OF PORPHYRINS [J].
CROSSLEY, MJ ;
KING, LG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (14) :920-922
[6]  
Furuta H, 2001, ANGEW CHEM INT EDIT, V40, P2323, DOI 10.1002/1521-3773(20010618)40:12<2323::AID-ANIE2323>3.0.CO
[7]  
2-F
[8]   Synthesis of triazole- and pyridine-bridged porphyrin-chlorin and porphyrin dimers [J].
Genady, AR ;
Gabel, D .
TETRAHEDRON LETTERS, 2003, 44 (14) :2915-2917
[9]   Dual luminophor pressure-sensitive paint:: III.: Application to automotive model testing [J].
Gouterman, M ;
Callis, J ;
Dalton, L ;
Khalil, G ;
Mébarki, Y ;
Cooper, KR ;
Grenier, M .
MEASUREMENT SCIENCE AND TECHNOLOGY, 2004, 15 (10) :1986-1994
[10]   TETRA(PENTAFLUOROPHENYL)PORPHOLACTONE [J].
GOUTERMAN, M ;
HALL, RJ ;
KHALIL, GE ;
MARTIN, PC ;
SHANKLAND, EG ;
CERNY, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (10) :3702-3707