Reactions of 2,2,4,4‐Tetramethyl‐3‐methylenecyclobutylidene; Thermal Rearrangements of a 2‐Methylenebicyclo[2.1.0]pentane | Zendy

Brinker Udo H. | Zendy; Erdle Wolfgang | Zendy

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Reactions of 2,2,4,4‐Tetramethyl‐3‐methylenecyclobutylidene; Thermal Rearrangements of a 2‐Methylenebicyclo[2.1.0]pentane

Author(s) -

Brinker Udo H.,

Erdle Wolfgang

Publication year - 1987

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198712601

Subject(s) - pentane , thermal decomposition , carbene , chemistry , alkane , medicinal chemistry , stereochemistry , organic chemistry , photochemistry , hydrocarbon , catalysis

1,3‐Insertion in the CH bonds of the methyl groups in the carbene 1 leads to formation of the strained 2‐methylenebicyclo[2.1.0]pentane 2 as main product. Also formed are 3 and possibly the [l.l.l]propellane4, evidence for which, however, is provided only by the secondary product 5. The thermolysis of 2 affords the first activation parameters for this class of compounds.

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