1,3‐Dipolar  cycloaddition  of nitrile oxides with symmetrical tri‐ and polycyclic strained olefins | Zendy

Darvatkar Nitin B. | Zendy; Wankhede Karuna S. | Zendy; Bhilare Sachin V. | Zendy; Deorukhkar Amol R. | Zendy; Raut Dilip G. | Zendy; Vaidya Vipraja V. | Zendy; Trivedi Girish K. | Zendy; Salunkhe Manikrao M. | Zendy

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1,3‐Dipolar cycloaddition of nitrile oxides with symmetrical tri‐ and polycyclic strained olefins

Author(s) -

Darvatkar Nitin B.,

Wankhede Karuna S.,

Bhilare Sachin V.,

Deorukhkar Amol R.,

Raut Dilip G.,

Vaidya Vipraja V.,

Trivedi Girish K.,

Salunkhe Manikrao M.

Publication year - 2010

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.421

Subject(s) - benzonitrile , chemistry , nitrile , cycloaddition , oxide , 1,3 dipolar cycloaddition , double bond , dipole , 2 norbornyl cation , computational chemistry , organic chemistry , stereochemistry , catalysis

1,3‐Dipolar cycloadditions of benzonitrile oxide and carbethoxyformonitrile oxide (CEFNO) with various facially perturbed polycyclic symmetrical dienophiles ( 1 , 1a , 1b , 2 , 2a , 2b , 3 , 3b , 4 , 5 , 6 ) were investigated. Cycloadditions took place chemoselectively at the norbornyl double bond and were found to be exclusively exo. Cycloadditions of benzonitrile oxide with dienophiles 4 and 5 led to mixture of inseparable products, however, that with CEFNO gave single products. Cycloadduct of dienophile 5 with CEFNO was found to be unstable, and it readily isomerized to more stable aromatic form. J. Heterocyclic Chem., (2010).

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