Iodomethylation

PEROXIDES AND PEROXIDE COMPOUNDS - ORGANIC PEROXIDES] (Vol 18) cis-4-Hydroxymethyl-2-iodomethyl-l,3-dioxolane [61508-55-2]... 

Chloromethyl anthracene [24463-19-2] M 226.7, m 141-142° dec, 141-142.5°. If it is free from OH in the IR then recryst from hexane- C6H6 or C6H6 as needles. If OH is present then some solvolysis has occurred. In this case treat 8.5g with SOCI2 (4.8g) in dioxane (60mL) and reflux for 5h, then evaporate to dryness and wash the residue with cold and recrystallise. With KI/Me2CO it forms the iodomethyl... 

Blanchard and Simmons suggested that the stable organozinc intermediate obtained in this reaction is probably bis-(iodomethyl) zinc zinc iodide (1). 

With 11/3-hydroxy steroids, 11/3, 19-ether formation competes with hemi-acetal formation.This is a consequence of steric hindrance of the 11/5-oxygen by the C-18 and C-19 iodomethyl groups which reduces the rate of hypoiodite formation [(3) (5)] even though the conformation of the... 

Bis-(iodomethyl)zinc-zinc iodide, 108 17 a,20 20,21-Bismethylenedioxy- U,2 -di-hydroxypregn-4-ene-3,11 -dione, 425 17a,20 20,21-Bismethylenedioxy-3,3-ethyl-enedioxy-5a,6a-oxidopregnan-l 1-one and 5 3,6p-oxide, 3... 

Reaction of 5-chloro-8-allyloxyquinoline with Br2 and I2 afforded 3-bromomethyl-, and 3-iodomethyl-8-chloro-2,3-dihydropyrido[l, 2, i-de -1,4-benzoxazinium salts (96MI2). Heating of 8-(2-chloroethoxy)quinolines in benzene and toluene gave 2,3-dihydropyrido[l,2,3- /e]-l,4-benzoxazinium chlorides (97MIP15). 

Halocyclization of 8-(allylamino)quinolines 408 with I2 afforded 3-iodomethyl-2,3-dihydro-l//-pyrido[l,2,3-[Pg.318]

Chemical Name 2/3-N-Diethvlaminoethylthio-4-p-phenylthiophenyl-3H-1,5-benzodiazepine iodomethylate... 

The corresponding 4-(iodomethyl)-l,4-dihydropyridine undergoes rapid transformation to the 4//-azepine 2 under milder conditions (e.g., on a silica gel column or on a TLC plate).120 4//-Azepines are also formed by the ring expansion of 4-(chloromethyl)-l,4-dihydropyridines with a variety of other nucleophiles, but, in general, are not isolated since they readily suffer addition of the nucleophile to yield 4-substituted 4,5-dihydro-l//-azepines.120 121-132... 

In the case of a-chloroalkyl aryl sulphoxides, the chloroalkyl group is easily replaced by an alkyl or aryl group of a Grignard reagent (equation 370). Bromomethyl sulphoxides react slowly and give the products in low yields, while iodomethyl sulphoxides are unreactive presumably due to steric hindrance (Table 29)678. 

Treatment of a-sulfonyl carbanion with (iodomethyl)trimethylsilane gave / -trimethylsilyl sulfones289-291. Alkylation of / -trimethylsilyl sulfones 235 gave various /Mrimethylsilyl sulfones292. The use of (iodomethyl)tributylstannane instead of (iodomethyl)trimethylsilane was shown to afford a tributylstannanyl derivative293. This compound has been used for syntheses of terminal olefins289-293. 

Halo-ethers can be formed by the reaction of alkenyl alcohols with various reagents. Hept-6-en-l-ol reacts with (collidine)2l PFg, for example, to form 2-iodomethyl-1 -oxacycloheptane. ... 

C2KH21IN2O4 67977-89-3) see Latamoxef iodomethyl penicillanate 5,.S-dioxide (C,H 2lN05S 76247-39-7) see Sultamicillin iodomethyl pivalate... 

Oxepanes have been obtained by the iodoetherification of unsaturated alcohols using bis(5 / -collidine)iodine(I) hexafluorophosphate <96JOC5793>. Thus 6-hepten-l-ol affords 2-iodomethyloxepane in 95% yield. A similar reaction with, for example, (3Z,6Z)-3,6-octadien-l-ol affords 2-(iodomethyl)-2-methyl-4-oxepane. 

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