The Formation of CC Bonds with the Aid of α‐Halogeno Ethers, Sulfides, and Amines

Abstract

New M e t h o d s of P r e p a r a t i v e O r g a n i c C h e m i s t r y VI'**]The Formation of C-C Bonds with the Aid of Ct-Halogeno Ethers, Sulfides, and Amines BY H. GROSS AND E. HoFT [*IDedicated to Professor Alfred Rieche on the occasion of his 65th birthday a-Halogeno ethers, sulfides, and amines are reactive compounds which can be used for the formation of new C-C bonds, either as nucleophilic or as electrophilic reagents, or by a-elimination. The use of these compounds in the synthesis of many classes of organic compounds is reviewed.a-Halogeno ethers, sulfides, and amines can be formally derived from, and are generally prepared from, carbonyl compounds. Whereas a-halogeno ethers and sulfides may be regarded as homopolar compounds as indicated in formula ( I a), the a-halogeno amines, according to Bohme 121, exist largely as resonancestabilized carbenium-immonium salts corresponding to formula (2b).

New Synthesis of Isoprene Based on Formaldehyde and Isobutylene

“…No added catalyst was required in that solvent; however, conversions were low. The literature on this addition reaction was recently reviewed (Gross and Hoft, 1967).…”

Kinetic Study of Synthesizing Dialkoxymethane Using 4-(Trialkylammonium) Propansultans as New Phase-Transfer Catalysts

“…The concentration of the active catalyst Q 0 OR, which was measured by the Hoffmann elimination method during the reaction, is shown in Figure 1. The concentration of Q 0 OR was determined by the principle of Hoffmann elimination (Gross and Flute, 1967;Lopez et al, 1989;Summers, 1955). Gas chromatography was carried out for the sake of analyzing the tertiary amine as It remains at a constant value after one minute of reaction or less.…”