Tetrahedron Letters

Iodotrimethylsilane deoxygenation of carbonyl conjugated allylic ethers

DA Hartman, RW Curley

Index: Hartman, David A.; Curley, Robert W. Jr. Tetrahedron Letters, 1989 , vol. 30, # 6 p. 645 - 646

Full Text: HTML

Citation Number: 7

Abstract

Abstract The attempted demethylation of 4-methoxy-β-ionone 1 3) δ 1.00, 1.03 (2s, 6, C (CH 3) 2), 1.3–1.7 (m, 4, CH 2), 1.77 (s, 3, 5CH 3), 2.27 (s, 3H, 9CH 3) 3.36 (s, 3, OCH 3), 3.48 (m, 1, 4H), 6.10 (d, 1, 8H, J= 16.5 Hz), 7.16 (d, 1, 7H, J= 16.5 Hz). 1) with iodotrimethylsilane gave the unexpected product, β-ionone (2). This reagent may prove useful in the cleavage of allylic ethers conjugated to ketones.

Related Articles:

Nickel-catalyzed oxidation of allylic alcohols with K2S2O8.

[Yamazaki, Shigekazu; Yamazaki, Yasuyuki Chemistry Letters, 1989 , p. 1361 - 1364]

Accurate measurements of 13C-13C J-couplings in the rhodopsin chromophore by double-quantum solid-state NMR spectroscopy

[Lai, Wai Cheu; McLean, Neville; Gansmueller, Axel; Verhoeven, Michiel A.; Antonioli, Gian Carlo; Carravetta, Marina; Duma, Luminita; Bovee-Geurts, Petra H. M.; Johannessen, Ole G.; De Groot, Huub J. M.; Lugtenburg, Johan; Emsley, Lyndon; Brown, Steven P.; Brown, Richard C. D.; DeGrip, Willem J.; Levitt, Malcolm H. Journal of the American Chemical Society, 2006 , vol. 128, # 12 p. 3878 - 3879]

A mild and efficient method for selective cleavage of ketals and acetals using lithium chloride in water-dimethyl sulfoxide

[Mandal, Pijus Kumar; Dutta, Pinak; Roy, Subhas Chandra Tetrahedron Letters, 1997 , vol. 38, # 41 p. 7271 - 7274]

A Sequence of Attaching the Unit CH2CH2COCH3 to 2, 2, 6-Trimethylcyclohexanone

[Breining, Tibor; Schmidt, Cirill; Polos, Katalin Synthetic Communications, 1987 , vol. 17, # 1 p. 85 - 88]

SYNTHESIS OF β-IONONE#

[Vani; Chida; Srinivasan; Chandrasekharam; Singh Synthetic Communications, 2001 , vol. 31, # 2 p. 219 - 224]

More Articles...