Evidence for a metastable trans-cycloalkene intermediate in the photochemistry of 1,1,4,4-tetramethyl-1,4-disilacyclohept-2-ene

Steinmetz, Mark G.; Seguin, K. J.; Udayakumar, B. S.; Behnke, J.

doi:10.1021/ja00174a022

Cited by 18 publications

(1 citation statement)

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“…One class comprises the transformations unstrained alkenes undergo, such as reactions with acids, [3][4][5] dihydroxylations, 5,6 and epoxidations. 7 The second class includes pericyclic reactions, [8][9][10] particularly cycloadditions with 1,3-dipoles or dienes, 1,3,[11][12][13][14][15][16][17][18][19][20][21] that often require strain to make them possible. Although strain-promoted cycloadditions have emerged as important transformations in synthesis 22 and chemical biology, 23 the scope of the reactivity of trans-cycloalkenes beyond these two classes remains limited.…”

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Reactivity of Seven-Membered-Ring trans-Alkenes with Electrophiles

Sanzone

Woerpel

2017

Synlett

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Seven-membered-ring trans-alkenes containing a silicon–oxygen bond reacted rapidly with oxygen gas and electron-deficient alkenes and alkynes to give products with high selectivity. Addition of an electron-donating substituent or incorporating additional strain increased the reactivity by over two orders of magnitude. These results indicate that release of strain is not the only driving force for reactivity.

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confidence: 99%

Reactivity of Seven-Membered-Ring trans-Alkenes with Electrophiles

Sanzone

Woerpel

2017

Synlett

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The Photochemistry of Organosilicon Compounds

Brook

2009

Patai's Chemistry of Functional Groups

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Introduction Compounds Containing a Single Silicon Atom Compounds Containing Two Silicon Atoms Disilanes Tri‐, Tetra‐ and Polysilanes Acylsilane Photochemistry Silyldiazoalkanes and Silylcarbenes Photochemical Routes to Silenes, Silylenes and Disilenes Photochemical Rearrangements of Silenes, Silylenes and Disilenes Other Photolyses Leading to Multiply Bonded Silicon Photolysis of Miscellaneous Compounds Addendum Photochemical Routes to Silenes, Silylenes and Disilenes Summary

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