Gutsche formation

Wei phaar, R., Gutsche, B. (2002). Formation of acrylamide in heated potato products -model experiments pointing to asparagine as precursor-. Deutsche Lebensmittel-Rundschau, 98, 591-400. 

Much interest has centred on the branch of cyclophanes known as calixarenes. They are polyphenol systems that can act as hosts in the formation of inclusion compounds, where a small guest molecule resides completely in a cavity within a single host they are cone-shaped cavitands . Several accounts have appeared of their history. The discovery by Baeyer of a formaldehyde/phenol resin led to Bakelite and to the work of A. Zincke and E. Ziegler, who gave to the first oligomer a tetrameric structure of a calix[4]arene. Later syntheses by Gutsche (1978) led to calixarenes with 4, 6 or 8 phenol residues.107-109... 

Two ring enlargements of this type are described in Organic Syntheses, namely the formation of cycloheptanone from cyclohexanone (33-36% yield) by de Boer and Bakker (1963) and of 2-phenylcycloheptanone from cyclohexanone and phenyldiazo-methane (41-46% yield) by Gutsche and Johnson (1963). 

Gutsche, C.D. Filling the Baskets Complex Formation with Calixarenes. In Calixarenes Monograph in Supra-molecular Chemistry Royal Society of Chemistry Cambridge, 1989 Vol. 1. 149-185. 

Alkylation of 14 with PicCl-HCl (2 equiv.) in the presence of BaO/Ba(OH)2 affords regioselectivity the barium complex of 1,4-diether 16a in 80% yield [23]. The formation of a labile K complex has been hypothesized by Gutsche to account for the selective 1,4-di-O-alkylation of 14 when using Me3SiOK, Me3COK, or KH as the base [22]. 

T. Koenig, B. Gutsche, M. Hartl, R. Huebscher, P. Schreier, and W. Schwab, 3-Hydroxy-4,5-dimethyl-2(5H)-furanone (sotolon) causing an off-flavor elucidation of its formation pathways during storage of citrus soft drinks, J. Agric. Food Chem. 47 3288 (1999). 

---