A facile method for the synthesis of (2R,3R)-1,4-dimethoxy-1,1,4,4- tetrasubstituted-2,3-butanediols involving oxidative cleavage of benzylidene acetal as a key step is described. These sterically hindered diols unusually formed cyclic sulfites as the major product under methanesulfonylation reaction conditions. Copyright © Taylor & Francis Group, LLC.

Balasubramanian Viswanathan

Thirukkallam Kanthadai Varadarajan

BUTANEDIOL

SULFITE

article

chemical modification

chemical reaction

oxidation kinetics

Sulfonation

synthesis

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IIT Madras

Facile Synthesis and Unusual Methanesulfonylation Reaction of (2R,3R)‐1,4‐Dimethoxy‐1,1,4,4‐tetrasubstituted‐2,3‐butanediols

Synthetic Communications

The synthesis and crystal structure of macrocyclic Schiff bases formed in a short reaction time from (1R,2R)-diammoniumcyclohexane mono-(+)-tartrate were investigated. Microwave irradiation of a mixture of bis-(hydroxyaldehydes) and chiral diamines in the presence of potassium carbonate afforded chiral macrocyclic tetraimines in moderate good yields. The structure of the [2+2] macrocycle was confirmed by both MALDI-TOF analysis and single-crystal XRD. The X-ray crystallographic analysis of the unsolved macrocycle Schiff base grown from a hexane-ethyl acetate solution confirmed the cyclic nature of the structure. The macrocycle stack in an eclipsed manner along the crystallographic a-axis, giving rise to infinite columns with macropores. The results show that the crystal structure of the macrocycles resembles that of calixarene and exhibits columnar staking in the solid state.

Organic and Biomolecular Chemistry

Synthesis and crystal structure of [2 + 2] calixsalens

Microwave irradiation of various dialdehydes and chiral diamines afforded chiral macrocyclic imines in moderate to good yields. Linked dialdehydes predominantly form [2+2] macrocycles whereas dialdehydes without linkers yield [3+3] macrocycles. This is the first report of template-free synthesis of calixsalen-type macrocycles formed in shorter reaction times under microwave conditions. In all the reactions, the salts of chiral diamines were used in contrast to the free diamines normally employed. © 2005 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

Microwave assisted cyclocondensation of dialdehydes with chiral diamines forming calixsalen type macrocycles

Fuel

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Synlett

Novel Formation of Chloromethanesulfinates in the Methanesulfonylation Reaction of Hindered Alcohols

Journal of the Chemical Society, Perkin Transactions 1

Synthesis, structure and comparative stability of β-hydrazono, oximino methyl ether and imino boronates

Facile synthesis and unusual methanesulfonylation reaction of (2R,3R)-1,4-dimethoxy-1,1,4,4-tetrasubstituted-2,3-butanediols

Journal	Synthetic Communications
ISSN	00397911
Open Access	No