Abstract:The routes of transformation of the simplest bicyclopropylidene into the derivatives of the second and third generations and synthesis of perspirocyclopropanated [3]rotane and linear spiral [4] and [5]triangulanes are discussed.
“…The ratio of 729 to 469 depends on the reaction conditions employed. Several rationalizations of this surprisingly efficient [2 + 2] cycloaddition, which according to orbital symmetry conservation rules should not be a concerted reaction, have been published over the years. ,479a, 127 …”
Section: 4 Oligospirocyclopropanated Carbo- and
Heterocyclesmentioning
confidence: 99%
“…In most cases, substituted bicyclopropylidenes such as 751 upon heating gave complex mixtures of products like 752 − 755 (Scheme ) 501a. However, formation of a single product 757 was observed when 9-cyclopropylidenebicyclo[6.1.0]nonane 756 was heated at 100 °C (Scheme ); unfortunately, no stereochemical details have been reported for 757 …”
Section: 4 Oligospirocyclopropanated Carbo- and
Heterocyclesmentioning
“…The ratio of 729 to 469 depends on the reaction conditions employed. Several rationalizations of this surprisingly efficient [2 + 2] cycloaddition, which according to orbital symmetry conservation rules should not be a concerted reaction, have been published over the years. ,479a, 127 …”
Section: 4 Oligospirocyclopropanated Carbo- and
Heterocyclesmentioning
confidence: 99%
“…In most cases, substituted bicyclopropylidenes such as 751 upon heating gave complex mixtures of products like 752 − 755 (Scheme ) 501a. However, formation of a single product 757 was observed when 9-cyclopropylidenebicyclo[6.1.0]nonane 756 was heated at 100 °C (Scheme ); unfortunately, no stereochemical details have been reported for 757 …”
Section: 4 Oligospirocyclopropanated Carbo- and
Heterocyclesmentioning
The synthesis of
cis
‐1,2‐dialkylcyclopropan‐1‐ol by treatment of carboxylic acid esters with at least 2 equivalent of Grignard reagent and a catalytic or equivalent amount of titanium tetraisopropoxide is referred to as the Kulinkovich reaction. The study finds that this reaction proceeds through an intermediate of low‐ valency dialkoxytitanacyclopropane. This reaction has been extensively modified to various other conditions, such as amides, nitriles, lactones, etc. Several modifications have been applied for this reaction, which occur either catalytically or asymmetrically. This reaction has been used for the preparation of cyclopropanols and other noncyclopropyl products.
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