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Journal of The Chemical Society-perkin Transactions 1 | 1977

The photoaddition of aliphatic amines to benzene

Michael Bellas; Derek Bryce-Smith; Michael T. Clarke; Andrew Gilbert; Garune Klunkin; Stefan Krestonosich; Carl Manning; S. Wilson

Primary, secondary, and tertiary aliphatic amines undergo photoaddition to benzene via photoexcitation of benzene to the S1 state. Primary amines give products of 1,2-, 1,3-, and 1,4-addition of the N–H bond, although the 1,3-adducts are derived from secondary photoreactions of the 1,2-adducts by way of hexa-1,3,5-triene intermediates. Secondary amines react similarly, but give only 1,2- and 1,4-adducts. The photoadditions of tertiary amines involve an α-C–H bond in the amine and occur 1,4- to the benzene ring, but little addition occurs in the absence of methanol or other proton donors. The mechanisms of these reactions have been investigated, and the findings are discussed : charge-transfer processes and both polar and radical intermediates appear to be involved.


Journal of Organic Chemistry | 1981

Sigmatropic rearrangements of 1,1-diarylindenes. Migratory aptitudes of aryl migration in the ground and electronically excited states

Carl Manning; Michael R. McClory; John J. McCullough


Angewandte Chemie | 1974

Solid Phase Synthesis and Photochemistry of 4,4′‐Stil‐benedicarbaldehyde

Jack Y. Wong; Carl Manning; Clifford C. Leznoff


Canadian Journal of Chemistry | 1974

Photocyclization Reactions of Aryl Polyenes. VII. The Photocyclization of 1-Phenyl-4-thienyl- and 1,4-Dithienyl-1,3-butadienes

Clifford C. Leznoff; Wolfgang Lilie; Carl Manning


Angewandte Chemie | 1974

Festphasensynthese und Photochemie von 4,4′-Stilbendicarbaldehyd†

Jack Y. Wong; Carl Manning; Clifford C. Leznoff


Canadian Journal of Chemistry | 1975

Photocyclization Reactions of Aryl Polyenes. IX. The Photocyclization of Stilbenecarboxaldehydes and 1-Formylphenyl-4-phenyl-1,3-butadienes

Carl Manning; Clifford C. Leznoff


ChemInform | 1981

SIGMATROPIC REARRANGEMENTS OF 1,1-DIARYLINDENES. MIGRATORY APTITUDES OF ARYL MIGRATION IN THE GROUND AND ELECTRONICALLY EXCITED STATES

Carl Manning; Michael R. McClory; John J. McCullough


ChemInform | 1979

Preparation and photochemistry of cyclohexene-1-carbonitriles

John J. McCullough; Carl Manning


ChemInform | 1978

THE PHOTOADDITION OF ALIPHATIC AMINES TO BENZENE

M. Bellas; Derek Bryce-Smith; M. T. Clarke; Andrew Gilbert; G. Klunkin; S. Krestonosich; Carl Manning; S. Wilson


ChemInform | 1975

PHOTOCYCLIZATION REACTIONS OF ARYL POLYENES PART 9, THE PHOTOCYCLIZATION OF STILBENECARBOXALDEHYDES AND 1-FORMYLPHENYL-4-PHENYL-1,3-BUTADIENES

Carl Manning; Clifford C. Leznoff

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S. Wilson

University of Reading

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