A Versatile Preparation of 2-Methyleneoxetanes

Dollinger, Lisa M.; Howell, Amy R.

doi:10.1021/jo9611733

Cited by 43 publications

(26 citation statements)

References 19 publications

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“…Solution IR spectra generally have carbonyl stretches in the 1820–1840 cm −1 . For example, the solution IR of β‐propiolactone has CO stretching peak at 1834 cm −1 , whereas the methyl‐substituted phenyl‐β‐lactone has a reported CO stretch of 1825 cm −1 , These values are 70–80 cm −1 lower than the predicted harmonic stretching frequencies. While the IR spectra for β‐propiolactone indicate a very large difference between gas phase and solution, the CO stretch for the gaseous molecule is still 30 cm −1 lower than predicted value.…”

Section: Experimental and Calculated Co Stretching Frequencies In Repmentioning

confidence: 91%

Infrared spectroscopic confirmation of α‐lactone formation in the dissociation of a gaseous amino acid

Wenthold

Koirala

Somogyi

et al. 2016

J of Physical Organic Chem

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The product obtained upon collision-induced dissociation of sulfonated phenylalanine in the gas phase has been investigated by using infrared multiphoton dissociation spectroscopy with a free-electron laser. This confirms that the product formed by loss of ammonia from the amino acid is the α-lactone, as had been deduced previously based on qualitative analysis and electronic structure calculations. Spectroscopically, the structure is confirmed by the presence of the carbonyl stretching peak at 1915 cm À1 and supported by excellent agreement between the predicted and observed S-O stretching bands. The agreement between predicted relative intensities is not as good, but can be attributed to the nonlinear process of IRMPD.

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Section: Experimental and Calculated Co Stretching Frequencies In Repmentioning

confidence: 91%

Infrared spectroscopic confirmation of α‐lactone formation in the dissociation of a gaseous amino acid

Wenthold

Koirala

Somogyi

et al. 2016

J of Physical Organic Chem

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“…With no further investigations reported for over 20 years, in 1996 Dollinger and Howell 456 reported a new approach to 2methyleneoxetanes through methylenation of β-lactones (Scheme 111). Good yields were achieved with the Petasis reagent to generate varied substituted methyleneoxetanes, whereas with the more Lewis acidic Tebbe reagent the product could not be isolated.…”

Section: Survey Of Oxetanes In Drug Discovery Patentsmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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“…Only the 4-exoproducts 14 and 16 were isolated. Dienol 15, which allowed for 4-exo-or 6-endo-product formation, also gave exclusively 4-exoproduct (18). However, a 4-exo-vs. 5-endo-competition experiment was not reported.…”

Section: Resultsmentioning

confidence: 97%