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Synlett

Volumn , Issue 5, 2008, Pages 659-662

Microwave-assisted reactions of α-diazosulfoxides to form α-oxosulfines

(3) O'Sullivan, Orlagh C M a Collins, Stuart G a Maguire, Anita R a

a UNIVERSITY COLLEGE CORK (Ireland)

Author keywords

Diazosulfoxides; Diels Alder cycloadditions; Microwave assisted reactions; Sulfine; Wolff rearrangement

Indexed keywords

ALPHA DIAZOSULFOXIDE DERIVATIVE; ALPHA OXOSULFINE DERIVATIVE; CLOROFENE; RHODIUM; SULFANILAMIDE DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLOADDITION; DECOMPOSITION; DIELS ALDER REACTION; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; WOLFF REARRANGEMENT; X RAY CRYSTALLOGRAPHY;

EID: 41349121415 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032105 Document Type: Article

Times cited : (17)

References (18)

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13
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- General Experimental Procedure The diazosulfoxide (20 mg, 1 equiv) and 2,3-dimethyl-1,3-butadiene (10 equiv) were dissolved in distilled CH 2Cl2 (2 mL) in a sealed 10 mL microwave vessel. A CEM Discover microwave was employed to irradiate the reaction mixtures to 135°C using a 3 min ramp and 7 min hold time. Reaction temperature was recorded using an IR sensor. The solvent was removed in vacuo and NMR spectra of the residues were recorded and used to obtain the ratio of cycloadducts formed in each experiment. Representative Spectral Data Cycloadduct 6: mp 164-166°C Anal. Calcd, ) for C14H20O3S: C, 62.66; H, 7.51. Found: C, 62.67; H, 7.48. IR (KBr, νmax, 1765 (C=O, 1023 (S=O) cm-1. 1H NMR (300.13 MHz, CDCl 3, δ= 1.15-2.17 (13 H, m, cyclohexyl ring and s at 1.73 for Me groups, 2.24-2.39 (1 H, m, cyclohexyl ring, 2.48 1 H, A of ABq, J, 17
- +: 269.1211; found: 269.1223.

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17
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- Sander, W.¹ Strehl, A.² Maguire, A.R.³ Collins, S.⁴ Kelleher, P.G.⁵

18
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- Diazosulfoxides 2 and 3 were reacted in diastereomerically pure form as illustrated in Scheme 1 and also as a mixture of diastereomers at sulfur with essentially the same results.
- Diazosulfoxides 2 and 3 were reacted in diastereomerically pure form as illustrated in Scheme 1 and also as a mixture of diastereomers at sulfur with essentially the same results.

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