134858-17-6

Basic information

• Product Name: Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaen-2-amine, N-(triphenylphosphoranylidene)-
• CAS NO: 134858-17-6
• Molecular Formula: C29H24NP
• Molecular Weight: 417.49
• Mol File: 134858-17-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaen-2-amine, N-(triphenylphosphoranylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaen-2-amine, N-(triphenylphosphoranylidene)-(134858-17-6)
• EPA Substance Registry System: Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaen-2-amine, N-(triphenylphosphoranylidene)-(134858-17-6)

Safety Data

• Hazardous Substances Data: 134858-17-6(Hazardous Substances Data)

Upstream product

• 134858-12-1 2-azido-1,6-methano<10>annulene 
• 603-35-0 triphenylphosphine 
• 15825-92-0 2-bromo-1,6-methano[10]annulene 
• 2443-46-1 1,6-methano[10]annulene 

Downstream Products

• 137594-11-7 C₂₉H₂₄NP 
• 137594-10-6 C₂₉H₂₄NP 

Relevant articles and documents

Synthesis of 1,6-Methanoannulenopyridines by Tandem Aza-Wittig Reaction/Electrocyclisation

Iminophosphoranes 1 (X = PPh3) derived from the corresponding 1,6-methanoannulenes have been made to react with isothiocyanates and also with aromatic aldehydes to give, by an aza-Wittig reaction followed by cyclisation, novel 1,6-methanoannulenopyridines of structural types 2 and 6.Aza-Wittig reactions of the 2-triphenylphosphoranylideneamino derivative 3 (x = PPh3) with aromatic aldehydes or isothtiocyanates led to the Schiff's bases 3 (X = CHAr) or carbodiimides (X = C=NAr) respectively.The latter on treatment with enamines gave, by a Diels-Alder cyclisation, the annulenopyridines 12.

The Synthesis of Novel N-Heterocycles from 2-Azido-, 2-Vinylazido- and 2-Formyl-1,6-Methanoannulene-2-carbaldehydes

The preparation of 2-azido-1,6-methanoannulene 2 from 2-lithioannulene is described.The annulene 2 underwent ring expansion on thermolysis in the presence of various secondary amines to give novel bridged aza-annulenes of type 3 and also gave 1,3-dipolar addition products.When heated the vinyl azides 13 (R1 = R2 = H) and 13 underwent cyclisation to give the annulenopyrroles 14 and 15 respectively.Annulenopyridines such as 18 were obtained from the iminophosphorane 16 via an aza-Wittig reaction with phenyl or allyl isothiocyanate or tolyl isocyanate.Some 2-formyl derivatives 1 (R1 = CHO) when treated with tosylmethyl isocyanide yielded oxazolylannulenes 19.