scholarly journals Frequency Doubled CO2 Laser Induced Decomposition of Carbonyl Compounds: Cyclobutanone

1984 ◽  
Vol 4 (1-6) ◽  
pp. 275-285 ◽  
Author(s):  
Mei-Kuen Au ◽  
P. A. Hackett ◽  
M. Humphries ◽  
P. John

This paper reports the first use of radiation derived from a TEA carbon dioxide laser by nonlinear upshifting techniques (second harmonic generation) in initiating multiphoton absorption and dissociation. The frequency doubled CO2 laser has frequency coverage from 2180–1750 cm–1. This frequency region is of importance as it allows pumping of the fundamental stretching modes of organic carbonyl groups (anhydrides, acyl chlorides and strained cyclic ketones), inorganic carbonyl groups, and carbontritium bonds. The laser has been used to excite cyclobutanone in the region of the carbonyl stretch. Efficient multiphoton absorption and two channel dissociation are observed. The product array is consistent with that observed upon excitation at 10 μm.

2006 ◽  
Vol 18 (14) ◽  
pp. 1533-1535 ◽  
Author(s):  
D.C. Dai ◽  
S.J. Xu ◽  
S.L. Shi ◽  
M.H. Xie ◽  
C.M. Che

2000 ◽  
Vol 78 (9) ◽  
pp. 1194-1203
Author(s):  
Paul C Venneri ◽  
John Warkentin

A cyclopropanone, a cyclopropenone, cyclobutanones, a cyclobutane-1,3-dione, and a cyclobutene-1,2-dione reacted with dimethoxycarbene to afford acetals of the next larger ring by formal insertion of the carbene into a C—C bond α to the carbonyl group. When either of two saturated α-ring carbons could be involved in the process, the ring expansion was selective, affording primarily the product of apparent insertion into the more substituted ring bond. With 2,3-dimethoxycyclobutene-1,2-dione, insertion occurred between the carbonyl groups and with β-propiolactone it occurred at the lactone bond. β-Propiolactam, however, reacted by insertion of the carbene into the N—H bond.Key words: β-propiolactone, cyclobutanone, cyclobutananedione, cyclopropanone, dialkoxycarbene.


Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1810-1814 ◽  
Author(s):  
Enoch A. Mensah ◽  
Shawn D. Green ◽  
Jesse West ◽  
Tyler Kindoll ◽  
Brenda Lazaro-Martinez

The development of a new, highly efficient, and simple method for masking carbonyl groups as acetals and ketals is described. This methodology relies on the nature of the palladium catalyst to direct the acetalization/ketalization reaction. This new protocol is mild and proceed with a very low catalyst loading at ambient temperatures. The method has been extended to a wide variety of different carbonyl compounds with various steric encumbrances to form the corresponding acetals and ketals in excellent yields.


Synthesis ◽  
2020 ◽  
Vol 52 (15) ◽  
pp. 2190-2195 ◽  
Author(s):  
Mikhail Krasavin ◽  
Alexander Safrygin ◽  
Olga Bakulina ◽  
Dmitry Dar’in

The earlier described reaction of homophthalic anhydrides with aromatic ketones and ammonium acetate was tested for cyclic ketones (yielding spirocyclic motifs) and aliphatic aldehydes. In contrast to previous findings, the reaction was found to require no catalyst at all and to be applicable, in the non-catalyzed format, to these new carbonyl substrates as well as aromatic ketones. The reaction typically proceeds with high diastereoselectivity; if not, the initial diastereomeric mixture can be quantitatively equilibrated into a single, trans-diastereomer on treatment with aqueous base.


1991 ◽  
Vol 113 (9) ◽  
pp. 3447-3450 ◽  
Author(s):  
Kenneth B. Wiberg ◽  
Louis S. Crocker ◽  
Kathleen M. Morgan

2000 ◽  
Vol 78 (11) ◽  
pp. 1396-1398 ◽  
Author(s):  
Moni Chauhan ◽  
Philip Boudjouk

A variety of α,β-unsaturated esters and cyclic ketones underwent smooth reduction of the carbon–carbon double bond with a combination of inexpensive and readily available trichlorosilane and CoCl2. The reactions are performed under very mild conditions and products are obtained in high yields.Key words: reduction, carbonyl compounds, trichlorosilane, ketones, chemoselectivity.


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