1,2,3,5-Tetrahydro-1,2,3-methenopentalene, a Valence Isomer of Isoindene: Synthesis and DielsâAlder Reactions This work was supported by the Fonds der Chemischen Industrie and by Chemetall GmbH. S.E.L. and D.D.P. thank Heriot-Watt University, Edinburgh, and the European Community for an Erasmus exchange scholarship. Dipl.-Chem. Patrick Musch assisted us in the performance of the quantum-chemical calculations.

Fischer, Thomas; Kunz, Ulrike; Lackie, Sarah E.; Cohrs, Carsten; Palmer, Daniel D.; Christl, Manfred

doi:10.1002/1521-3773(20020816)41:16<2969::aid-anie2969>3.0.co;2-1

Cited by 8 publications

(2 citation statements)

References 4 publications

(4 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The hydrogens on the C 8 C 9 double bond are also displaced in the endo direction. Similarly, Christl calculated a pyramidalization of 21.2° (at the UB3LYP/cc-pVDZ level) for the more strained tricyclo[3.1.0.0 2,6 ]hexene analogue 88 of 29 . In accord with expectations, 32 , the only π-facially dissymmetric constituent of the 222−211 series, is pyramidal (ψ = 7.6° in the exo direction with respect to the bicyclo[2.2.2]octadiene moiety).…”

Section: Resultsmentioning

confidence: 54%

Pyramidalized Olefins: A DFT Study of Bicyclo[2.1.1]-, -[3.2.1]-, and -[3.2.2]alkenes and Their Fused Derivatives. Two Rare Examples of π-Facially Symmetric Pyramidal Olefins

Williams

Margetić

2004

J. Org. Chem.

View full text Add to dashboard Cite

Density functional theory (B3LYP/6-31G) was used to study a large series of bridged polycyclic alkenes based on the bicyclo[2.1.1], -[3.2.1], and -[3.2.2] nuclei. In those compounds with pi-facial dissymmetry, butterfly bending of the strained olefinic bonds was generally predicted. Surprisingly, large pyramidalizations are calculated for the highly strained but pi-facially symmetric tetracyclo[5.1.1.1.(3,5)0(2,6)]dec-2-ene (28, psi = 19.8 degrees ) and tetracyclo[5.2.2.1.(3,5)0(2,6)]dodec-2,8,10-triene (33, psi = 14.4 degrees ). The preference for propano-directed bending in the bicyclo[3.2.1]octenes is about as strong as that for endo bending in norbornenes.

show abstract

Section: Resultsmentioning

confidence: 54%

Pyramidalized Olefins: A DFT Study of Bicyclo[2.1.1]-, -[3.2.1]-, and -[3.2.2]alkenes and Their Fused Derivatives. Two Rare Examples of π-Facially Symmetric Pyramidal Olefins

Williams

Margetić

2004

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…The formation of 20 may be mediated by initial generation of the zwitterionic intermediate 21 . The capacity of 21 for cyclization to the diazetidine gains support from the recent observation by the Christl group of the isomerization of 23 to 24 (Scheme ) 3 …”

mentioning

confidence: 85%

Contrasting Diastereofacial Selectivity Associated with N-Phenyltriazolinedione Cycloadditions to Oxaspirocycloheptatrienes

2002

View full text Add to dashboard Cite

show abstract

Desulfonylation Reactions

Alonso

Ájera

2009

Organic Reactions

View full text Add to dashboard Cite

The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon‐carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon‐carbon double bond when a β‐hydroxy or β‐alkoxy sulfone is employed. This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia‐type substrates (Julia‐Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

show abstract

Cited by 8 publications

References 4 publications

Pyramidalized Olefins: A DFT Study of Bicyclo[2.1.1]-, -[3.2.1]-, and -[3.2.2]alkenes and Their Fused Derivatives. Two Rare Examples of π-Facially Symmetric Pyramidal Olefins

Pyramidalized Olefins: A DFT Study of Bicyclo[2.1.1]-, -[3.2.1]-, and -[3.2.2]alkenes and Their Fused Derivatives. Two Rare Examples of π-Facially Symmetric Pyramidal Olefins

Contrasting Diastereofacial Selectivity Associated with N-Phenyltriazolinedione Cycloadditions to Oxaspirocycloheptatrienes

Desulfonylation Reactions

Contact Info

Product

Resources

About